Acetic Acid → HCID 21182319, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-4'-n-heptylbiphenyl (2.71 g) in tetrahydrofuran (100 ml) was added dropwise a solution of n-butyllithium in a mixture of diethyl ether and n-hexane (1.6M, 5.1 ml) at -78° C. After stirring at -78° C. for 30 minutes, the resultant mixture was added to a solution of diethyl oxalate (3.4 ml) in tetrahydrofuran (50 ml) at -78° C. The resultant mixture was allowed to warm to 0° C. for about 1 hour, and to the mixture was added acetic acid (0.5 ml). Evaporation gave a residue which was taken up into a mixture of water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation gave a residue which was chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (10:0-95:5, V/V) to give 1-Ethyl-2-(4-n-heptylphenyl)ethanedione (2.23 g).

Provenance & Evidence