Methyl vinyl ketone → HCID 12046648, compound

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Reaction Steps

A solution of (dimethyl-λ4-sulfanylidene)-acetic acid tert-butyl ester (6.3 g, 35.7 mmol) (CAS 195453-96-4; K. Saigo et al., J. Org. Chem. 2006, 71, 1633-1639) in dichloromethane (36 ml) was treated dropwise at 15° C. with but-3-en-2-one (2.64 g, 3.1 ml, 35.7 mmol) keeping the internal temperature below 27° C. The yellow mixture was stirred overnight at room temperature. For the workup, all volatiles were evaporated to give a yellow oil. The crude oil was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 80:20 as the eluent. The (1R,2R)-rel-2-acetyl-cyclopropanecarboxylic acid tert-butylester was obtained as a colorless oil (5.48 g, 83% yield). MS (ISP): m/z=185.0 [M+H]+.

Provenance & Evidence