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An Efficient Synthesis of 2-Diazo-2-(trimethylsilyl)ethanols and Their Application to Pyrazole Synthesis

Yoshiyuki Hari, Susumu Tsuchida, Ryosuke Sone, Toyohiko Aoyama*

*Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho, Nagoya 467-8603, Japan, Email:

Y. Hari, S. Tsuchida, R. Sone, T. Aoyama, Synthesis, 2007, 3371-3375.

DOI: 10.1055/s-2007-990817


The reaction of diazo(trimethylsilyl)methylmagnesium bromide with aldehydes or ketones gave 2-diazo-2-(trimethylsilyl)ethanols, which were applied to the synthesis of di- and trisubstituted pyrazoles via [3+2] cycloaddition reaction with ethyl propiolate or dimethyl acetylenedicarboxylate.

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Key Words

diazo alcohols, 2-diazo-2-(trimethylsilyl)ethanols, diazo(trimethylsilyl)methylmagnesium bromide, Huisgen Dipolar Cycloaddition, pyrazoles, trimethylsilyldiazomethane

ID: J66-Y2007-3570