Ethyl butyrate → Ethyl 2-formylbutanoate

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (10.1 g, 100 mmol) in THF (100 mL) was treated with n-butyllithium (1.6 M in hexane, 63 mL, 100 mmol) at room temperature under N2. The resulting pale yellow solution was cooled to −78° C. A solution of butyric acid ethyl ester (10.4 g, 89.2 mmol) in THF (28 mL) was added. Stirring was continued for a half hour at −78° C., after which ethyl formate (22.0 g, 300 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for three hours under N2. The reaction mixture was quenched with acetic acid (˜17 ml), diluted with diethyl ether, washed with water, brine, dried (Na2SO4). Silica gel chromatography (methyl acetate/hexane) provided 12.5 g of the title compound as a mixture of isomers.

Provenance & Evidence