Practical microwave synthesis for organic chemists: strategies, instruments, and protocols
"With the novice user in mind, this beginner's guide explains the basics behind microwave technology, evaluates available instruments and reaction modes, and provides practical hints for every eventuality. Includes 27 detailed protocols for often-used reactions."--BOOK JACKET.
Gespeichert in:
| Hauptverfasser: | , , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2009
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Zusammenfassung: | "With the novice user in mind, this beginner's guide explains the basics behind microwave technology, evaluates available instruments and reaction modes, and provides practical hints for every eventuality. Includes 27 detailed protocols for often-used reactions."--BOOK JACKET. |
| Beschreibung: | X, 299 S. Ill., graph. Darst. |
| ISBN: | 9783527320974 |
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| 245 | 1 | 0 | |a Practical microwave synthesis for organic chemists |b strategies, instruments, and protocols |c C. Oliver Kappe ; Doris Dallinger, and S. Shaun Murphree |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2009 | |
| 300 | |a X, 299 S. |b Ill., graph. Darst. | ||
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| 520 | 1 | |a "With the novice user in mind, this beginner's guide explains the basics behind microwave technology, evaluates available instruments and reaction modes, and provides practical hints for every eventuality. Includes 27 detailed protocols for often-used reactions."--BOOK JACKET. | |
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| adam_text | Contents
Preface IX
~ Microwave Synthesis — An Introduction 1
References 5
2 Microwave Theory 11
2.1 Microwave Radiation 11
2.2 Microwave Dielectric Hearing 12
2.3 Dielectric Properties 15
2.4 Microwave versus Conventional Thermal Heating 19
2.5 Microwave Effects 20
2.5.1 Temperature Momtonng in Microwave Chemistry 22
2.5.2 Thermal Effects (Kinetics) 28
2.5.3 Specific Microwave Effects 31
2.5.4 Non-Thermal (Athermal) Microwave Effects 37
References 42
3 Equipment Review 45
3.1 Introduction 45
3.2 Domestic Microwave Ovens 46
3.3 Dedicated Microwave Reactors for Orgamc Synthesis 47
3.4 Single-Mode Instruments 51
3.4.1 Biotage AB 51
3.4.1.1 Initiator Platform 51
3.4.1.2 Emrys Platform (2000-2004) 54
3.4.1.3 Chemspeed SWAVE 55
3.4.2 CEM Corporation 56
3.4.2.1 Discover Platform 56
3.4.2.2 ExplorerPLS Systems 58
3.4.2.3 Voyager Systems 58
3.4.2.4 Peptide Synthesizers 59
Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols
C. Oliver Kappe, Doris Dallinger, and S. Shaun Murphree
Copyright © 2009 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-32097-4
VI Contents
3.4.3 Milestone s.r.l. 62
3.5 Multimode Instruments 62
3.5.1 Anton Paar GmbH 62
3.5.1.1 Rotors and Vessels 64
3.5.2 Biotage AB 67
3.5.3 CEM Corporation 68
3.5.3.1 MARS Scale-Up System Accessories 69
3.5.3.2 MARS Parallel System Accessories 70
3.5.4 Milestone s.r.l. 72
3.5.4.1 MultiSYNTH System 73
3.5.4.2 MicroSYNTH Labstation 75
3.5.4.3 StartSYNTH 80
3.5.4.4 Scale-Up Systems 81
3.5.4.5 RotoSYNTH 84
References 85
4 Microwave Processing Techniques 87
4.1 Solvent-Free Reactions 87
4.2 Phase-Transfer Catalysis 91
4.3 Open- versus Closed-Vessel Conditions 94
4.4 Pre-Pressunzed Reaction Vessels 98
4.5 Non-Classical Solvents 102
4.5.1 Water as Solvent 102
4.5.2 Ionic Liquids 106
4.6 Passive Hearing Elements 112
4.7 Processing Techniques in Drug Discovery and High-Throughput
Synthesis 115
4.7.1 Automated Sequential versus Parallel Processing 116
4.7.2 High-Throughput Synthesis Methods 127
4.7.2.1 Solid-Phase Synthesis 128
4.7.2.2 Soluble Polymer-Supported Synthesis 131
4.7.2.3 Fluorous-Phase Organic Synthesis 133
4.7.2.4 Polymer-Supported Reagents, Catalysts and Scavengers 134
4.8 Scale-Up in Batch and Continuous Flow 138
4.8.1 Scale-Up in Batch and Parallel 141
4.8.2 Scale-Up Using Continuous Flow Techniques 143
4.8.3 Scale-Up Using Stop Flow Techniques 148
4.8.4 Flow-Through Techniques using Microreactors 150
References 153
5 Starting With Microwave Chemistry 161
5.1 Why Use Microwave Reactors? 161
5.2 Getting Started - Method Development 162
5.2.1 Open or Closed Vessels? 163
5.2.2 Choice of Solvent 165
Contents VII
5.2.3 Temperature, Time and Microwave Power 167
5.2.4 Microwave Instrument Software 172
5.2.5 Reaction Optrmization 173
5.3 Additional Aspects 176
5.3.1 Temperature Measurement 176
5.3.2 Simultaneous Cooling 177
5.3.3 Filling Volume 178
5.3.4 The Importance of Stirnng 179
5.3.5 Pressure Release 179
5.3.6 Inert Atmosphere ISO
5.3.7 Multiple Heating Steps 181
5.3.8 Reaction Monitoring 182
5.3.9 Reaction Scale versus Instrument 182
5.4 Equipment/Maintenance 184
5.5 General Suggestions 185
5.6 Safety Aspects 187
5.7 Advantages and Limitations 192
5.8 Frequently Asked Questions (FAQs) 194
References 200
6 Experimental Protocols 203
6.1 General Small-Scale Sealed-Vessel Microwave Processing 206
6.1.1 Organic Medium 206
6.1.1.1 Base-Catalyzed Ester Formation 206
6.1.1.2 Knoevenagel Condensation 209
6.1.1.3 Wüliamson Ether Synthesis 211
6.1.1.4 Grignard Reaction 213
6.1.1.5 Heck Reaction - Heterogeneous Catalyst 216
6.1.1.6 Oxidative Aromatization 218
6.1.1.7 Oxidation of Borneol 220
6.1.1.8 Diels-Alder Reaction 223
6.1.2 Low-Absorbing Organic Medium - Passive Heating Elements 225
6.1.2.1 N-AlkylationofPyrazole 225
6.1.3 Aqueous Medium 228
6.1.3.1 N-Acetylation of p-Chloroaniline 228
6.1.3.2 Dihydroindazolone Synthesis 231
6.1.4 Neat Reaction Medium 234
6.1.4.1 Imme Synthesis 234
6.1.4.2 N-Formylation of 2-Nitroaniline 236
6.2 Reaction Optimization 238
6.2.1 Empirical Optimization - Hydrolysis of Benzamide 238
6.2.2 Optimization using Statistical Methods (DoE) - Synthesis of
Monastrol 241
6.3 Library Generation 245
6.3.1 Automated Sequential Library Generation 245
VIII Contents
6.3.1.1 Hantzsch Synthesis 245
6.3.1.2 Biginelli Synthesis 249
6.3.2 Parallel Library Generation 254
6.3.2.1 Biginelli Synthesis 254
6.4 Reaction Scale-Up 258
6.4.1 Single Batch Mode 258
6.4.1.1 Synthesis of Aspirin on a 10 and 100 mmol Scale 258
6.4.1.2 Suzuki Reaction under Closed- and Open Conditions
(1.5, 15, 150 mmol) 261
6.4.2 ParaUel Scale-Up 266
6.4.2.1 Biginelli Reaction 266
6.4.3 Flow Mode 269
6.4.3.1 Fischer Indole Synthesis 269
6.5 Special Processing Techmques 272
6.5.1 Fractional Product Distilliation (Open-Vessel) 272
6.5.1.1 Pyranoqumolme Synthesis 272
6.5.2 Reactions with Gaseous Components 275
6.5.2.1 Ethoxycarbonylation with Carbon Monoxide 275
6.5.2.2 Ammocarbonylation with Molybdenum Hexacarbonyl 278
6.5.3 High-Temperature Processing 281
6.5.3.1 Hydrolysis of Ethyl Benzoate in Near-Cntical Water (NCW) 281
6.5.4 Solid-Phase Peptide Synthesis 284
6.5.4.1 Synthesis of a Nonapeptide 284
References 289
Index 291
|
| adam_txt |
Contents
Preface IX
~\ Microwave Synthesis — An Introduction 1
References 5
2 Microwave Theory 11
2.1 Microwave Radiation 11
2.2 Microwave Dielectric Hearing 12
2.3 Dielectric Properties 15
2.4 Microwave versus Conventional Thermal Heating 19
2.5 Microwave Effects 20
2.5.1 Temperature Momtonng in Microwave Chemistry 22
2.5.2 Thermal Effects (Kinetics) 28
2.5.3 Specific Microwave Effects 31
2.5.4 Non-Thermal (Athermal) Microwave Effects 37
References 42
3 Equipment Review 45
3.1 Introduction 45
3.2 Domestic Microwave Ovens 46
3.3 Dedicated Microwave Reactors for Orgamc Synthesis 47
3.4 Single-Mode Instruments 51
3.4.1 Biotage AB 51
3.4.1.1 Initiator Platform 51
3.4.1.2 Emrys Platform (2000-2004) 54
3.4.1.3 Chemspeed SWAVE 55
3.4.2 CEM Corporation 56
3.4.2.1 Discover Platform 56
3.4.2.2 ExplorerPLS Systems 58
3.4.2.3 Voyager Systems 58
3.4.2.4 Peptide Synthesizers 59
Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols
C. Oliver Kappe, Doris Dallinger, and S. Shaun Murphree
Copyright © 2009 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-32097-4
VI Contents
3.4.3 Milestone s.r.l. 62
3.5 Multimode Instruments 62
3.5.1 Anton Paar GmbH 62
3.5.1.1 Rotors and Vessels 64
3.5.2 Biotage AB 67
3.5.3 CEM Corporation 68
3.5.3.1 MARS Scale-Up System Accessories 69
3.5.3.2 MARS Parallel System Accessories 70
3.5.4 Milestone s.r.l. 72
3.5.4.1 MultiSYNTH System 73
3.5.4.2 MicroSYNTH Labstation 75
3.5.4.3 StartSYNTH 80
3.5.4.4 Scale-Up Systems 81
3.5.4.5 RotoSYNTH 84
References 85
4 Microwave Processing Techniques 87
4.1 Solvent-Free Reactions 87
4.2 Phase-Transfer Catalysis 91
4.3 Open- versus Closed-Vessel Conditions 94
4.4 Pre-Pressunzed Reaction Vessels 98
4.5 Non-Classical Solvents 102
4.5.1 Water as Solvent 102
4.5.2 Ionic Liquids 106
4.6 Passive Hearing Elements 112
4.7 Processing Techniques in Drug Discovery and High-Throughput
Synthesis 115
4.7.1 Automated Sequential versus Parallel Processing 116
4.7.2 High-Throughput Synthesis Methods 127
4.7.2.1 Solid-Phase Synthesis 128
4.7.2.2 Soluble Polymer-Supported Synthesis 131
4.7.2.3 Fluorous-Phase Organic Synthesis 133
4.7.2.4 Polymer-Supported Reagents, Catalysts and Scavengers 134
4.8 Scale-Up in Batch and Continuous Flow 138
4.8.1 Scale-Up in Batch and Parallel 141
4.8.2 Scale-Up Using Continuous Flow Techniques 143
4.8.3 Scale-Up Using Stop Flow Techniques 148
4.8.4 Flow-Through Techniques using Microreactors 150
References 153
5 Starting With Microwave Chemistry 161
5.1 Why Use Microwave Reactors? 161
5.2 Getting Started - Method Development 162
5.2.1 Open or Closed Vessels? 163
5.2.2 Choice of Solvent 165
Contents VII
5.2.3 Temperature, Time and Microwave Power 167
5.2.4 Microwave Instrument Software 172
5.2.5 Reaction Optrmization 173
5.3 Additional Aspects 176
5.3.1 Temperature Measurement 176
5.3.2 Simultaneous Cooling 177
5.3.3 Filling Volume 178
5.3.4 The Importance of Stirnng 179
5.3.5 Pressure Release 179
5.3.6 Inert Atmosphere ISO
5.3.7 Multiple Heating Steps 181
5.3.8 Reaction Monitoring 182
5.3.9 Reaction Scale versus Instrument 182
5.4 Equipment/Maintenance 184
5.5 General Suggestions 185
5.6 Safety Aspects 187
5.7 Advantages and Limitations 192
5.8 Frequently Asked Questions (FAQs) 194
References 200
6 Experimental Protocols 203
6.1 General Small-Scale Sealed-Vessel Microwave Processing 206
6.1.1 Organic Medium 206
6.1.1.1 Base-Catalyzed Ester Formation 206
6.1.1.2 Knoevenagel Condensation 209
6.1.1.3 Wüliamson Ether Synthesis 211
6.1.1.4 Grignard Reaction 213
6.1.1.5 Heck Reaction - Heterogeneous Catalyst 216
6.1.1.6 Oxidative Aromatization 218
6.1.1.7 Oxidation of Borneol 220
6.1.1.8 Diels-Alder Reaction 223
6.1.2 Low-Absorbing Organic Medium - Passive Heating Elements 225
6.1.2.1 N-AlkylationofPyrazole 225
6.1.3 Aqueous Medium 228
6.1.3.1 N-Acetylation of p-Chloroaniline 228
6.1.3.2 Dihydroindazolone Synthesis 231
6.1.4 Neat Reaction Medium 234
6.1.4.1 Imme Synthesis 234
6.1.4.2 N-Formylation of 2-Nitroaniline 236
6.2 Reaction Optimization 238
6.2.1 Empirical Optimization - Hydrolysis of Benzamide 238
6.2.2 Optimization using Statistical Methods (DoE) - Synthesis of
Monastrol 241
6.3 Library Generation 245
6.3.1 Automated Sequential Library Generation 245
VIII Contents
6.3.1.1 Hantzsch Synthesis 245
6.3.1.2 Biginelli Synthesis 249
6.3.2 Parallel Library Generation 254
6.3.2.1 Biginelli Synthesis 254
6.4 Reaction Scale-Up 258
6.4.1 Single Batch Mode 258
6.4.1.1 Synthesis of Aspirin on a 10 and 100 mmol Scale 258
6.4.1.2 Suzuki Reaction under Closed- and Open Conditions
(1.5, 15, 150 mmol) 261
6.4.2 ParaUel Scale-Up 266
6.4.2.1 Biginelli Reaction 266
6.4.3 Flow Mode 269
6.4.3.1 Fischer Indole Synthesis 269
6.5 Special Processing Techmques 272
6.5.1 Fractional Product Distilliation (Open-Vessel) 272
6.5.1.1 Pyranoqumolme Synthesis 272
6.5.2 Reactions with Gaseous Components 275
6.5.2.1 Ethoxycarbonylation with Carbon Monoxide 275
6.5.2.2 Ammocarbonylation with Molybdenum Hexacarbonyl 278
6.5.3 High-Temperature Processing 281
6.5.3.1 Hydrolysis of Ethyl Benzoate in Near-Cntical Water (NCW) 281
6.5.4 Solid-Phase Peptide Synthesis 284
6.5.4.1 Synthesis of a Nonapeptide 284
References 289
Index 291 |
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| id | DE-604.BV035048713 |
| illustrated | Illustrated |
| index_date | 2024-07-02T21:55:47Z |
| indexdate | 2024-07-09T21:21:01Z |
| institution | BVB |
| isbn | 9783527320974 |
| language | English |
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| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Kappe, Christian Oliver 1965- Verfasser (DE-588)130218464 aut Practical microwave synthesis for organic chemists strategies, instruments, and protocols C. Oliver Kappe ; Doris Dallinger, and S. Shaun Murphree Weinheim WILEY-VCH 2009 X, 299 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier "With the novice user in mind, this beginner's guide explains the basics behind microwave technology, evaluates available instruments and reaction modes, and provides practical hints for every eventuality. Includes 27 detailed protocols for often-used reactions."--BOOK JACKET. Microwave devices Organic compounds Synthesis Mikrowelle (DE-588)4039246-6 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s Mikrowelle (DE-588)4039246-6 s DE-604 Dallinger, Doris Verfasser aut Murphree, Shaun Verfasser aut HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016717424&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Kappe, Christian Oliver 1965- Dallinger, Doris Murphree, Shaun Practical microwave synthesis for organic chemists strategies, instruments, and protocols Microwave devices Organic compounds Synthesis Mikrowelle (DE-588)4039246-6 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4039246-6 (DE-588)4075695-6 |
| title | Practical microwave synthesis for organic chemists strategies, instruments, and protocols |
| title_auth | Practical microwave synthesis for organic chemists strategies, instruments, and protocols |
| title_exact_search | Practical microwave synthesis for organic chemists strategies, instruments, and protocols |
| title_exact_search_txtP | Practical microwave synthesis for organic chemists strategies, instruments, and protocols |
| title_full | Practical microwave synthesis for organic chemists strategies, instruments, and protocols C. Oliver Kappe ; Doris Dallinger, and S. Shaun Murphree |
| title_fullStr | Practical microwave synthesis for organic chemists strategies, instruments, and protocols C. Oliver Kappe ; Doris Dallinger, and S. Shaun Murphree |
| title_full_unstemmed | Practical microwave synthesis for organic chemists strategies, instruments, and protocols C. Oliver Kappe ; Doris Dallinger, and S. Shaun Murphree |
| title_short | Practical microwave synthesis for organic chemists |
| title_sort | practical microwave synthesis for organic chemists strategies instruments and protocols |
| title_sub | strategies, instruments, and protocols |
| topic | Microwave devices Organic compounds Synthesis Mikrowelle (DE-588)4039246-6 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Microwave devices Organic compounds Synthesis Mikrowelle Organische Synthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016717424&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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