Ethyl bromopyruvate → 2-Methylpentane

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Reaction Steps

Ethyl 3-bromo-2-oxopropanoate (6.76 mL) was added very carefully to a stirred solution of pentanethioamide (example 78, step e) (6.30 g) in ethanol (100 mL). The solution was then heated at reflux for 16 h. After cooling, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and evaporated in vacuo. Purification by silica gel chromatography eluting with 1:6 ethyl acetate: isohexane gave the subtitled compound as a yellow oil. Yield 6.5 g.

Provenance & Evidence