Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

被引：50

作者：

Dallinger, Doris ^{[1
]}

Pinho, Vagner D. ^{[1
]}

Gutmann, Bernhard ^{[2
]}

Kappe, C. Oliver ^{[1
]}

机构：

[1] Graz Univ, Inst Chem, NAWI Graz, Heinrichstr 28, A-8010 Graz, Austria

[2] Res Ctr Pharmaceut Engn GmbH RCPE, Inffeldgasse 13, A-8010 Graz, Austria

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 14期

关键词：

PALLADIUM-CATALYZED CYCLOPROPANATION; IN-TUBE REACTOR; CONTINUOUS-FLOW SYNTHESIS; DIAZO-COMPOUNDS; CARBOXYLIC-ACIDS; SITU GENERATION; AMINO-ACIDS; CYCLOADDITION; CHEMISTRY; PYRAZOLES;

D O I：

10.1021/acs.joc.6b01190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A configurationally simple and robust semi batch apparatus for the in situ on-demand generation of anhydrous solutions of diazomethane (CH2N2) avoiding distillation methods is presented. Diazomethane is produced by base-mediated decomposition of commercially available Diazald within a semipermeable Teflon AF-2400 tubing and subsequently selectively separated from the tubing into a solvent-and substrate-filled flask (tube-in-flask reactor). Reactions with CH2N2 can therefore be performed directly in the flask without dangerous and labor-intensive purification operations or exposure of the operator to CH2N2. The reactor has been employed for the methylation of carboxylic acids, the synthesis of alpha-chloro ketones and pyrazoles, and palladium-catalyzed cyclopropanation reactions on laboratory. The implementation of in-line FTIR technology allowed monitoring of the CH2N2 generation and its consumption. In addition, larger scales (1.8 g diazomethane per hour) could be obtained via parallelization (numbering up) by simply wrapping several membrane tubings into the flask.

引用

页码：5814 / 5823

页数：10

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