Ethyl butyrate → Ethyl 2-ethyl-3,3-bis(4-fluorophenyl)-3-hydroxypropionate

Participants

Reaction Conditions

Reaction Steps

Butyl lithium (65.7 mL of 2.1M solution, 138 mmol) was added to a solution of N-isopropylcyclohexylamine in 100 mL tetrahydrofuran at -20° C. After stirring for 1 hour and cooling to -40° C., ethyl butyrate (16.0 g, 138 mmol) was added. After stiring for an additional hour and further cooling to -70° C., 4,4'-difluorobenzophenone (15 g, 68.8 mmol) was added. The solution was stirred for 3 hours at -70° C., allowed to warm to 20° C. during the next 5 hours and stirred at 20° C. for 8 hours. The reaction was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried and concentrated in vacuo. The residue was crystallized from hexane to give 11.7 g of the title compound; m.p. =99°-101° C.

Provenance & Evidence