Ethyl chloroformate → 3-(4-Chlorophenyl)prop-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared according to the general procedure described by K. Ishizumi et al. (Chem. Pharm. Bull., 1968, 16, 492-497). A solution of ethyl chloroformate (5.2 mL, 55 mmol) in THF (15 mL) was added over 30 min to a solution of 4-chlorocinnamic acid (10 g, 55 mmol) and TEA (7.6 mL, 55 mmol) in THF (80 mL) while cooled to −5° C. The reaction was stirred for another 30 min at 0° C. and then sodium borohydride (4.2 gm, 110 mmol) was added. After 30 min., the reaction was slowly quenched with 2N hydrochloric acid and extracted twice with methylene chloride. The organic layers were washed with a portion of brine containing some aq. sodium bicarbonate, dried over sodium sulfate, and evaporated to give the title compound as a white solid. 1HNMR (CDCl3): δ 4.345 (dd, J=1.5 and 5.7 Hz, 2H), 6.36 (dt, J=5.7 and 15.8 Hz, 1H), 6.59 (br dt, J=1.5 and 15.8 Hz, 1H), 7.32 (Abq, 4H).

Provenance & Evidence