Oxalyl chloride → (E)-4-(diMethylaMino)but-2-enoyl chloride

Participants

Reaction Conditions

Reaction Steps

A well stirred suspension of 4-dimethylaminocrotonic acid hydrochloride (5.0 g, 30 mmol) in cold (0° C.) THF (40 mL) and DMF (2 pipet drops) is treated with oxalyl chloride (3.15 mL, 36 mmol). Stirring at 20–25° C. for 3 hours is followed by cooling to 0° C. and holding for 30 minutes. Solids are collected on a Buchner funnel (under a blanket of nitrogen) and the cake is washed with cold (0° C.) THF (3×5 mL). The solid is dried under vacuum (˜1 torr) at 40–50° C. for 3 hours to give 4.0 g of 4-dimethylaminocrotonoyl chloride hydrochloride. This material is characterized as its methyl ester by treatment of the solid with methanol.

Provenance & Evidence