Ammonium Chloride → cis-[3-(3-Diphenylcarbamoyloxypropenyl)phenoxy]acetic acid tert-butyl ester

Participants

Reaction Steps

2.0 M Lithium diisopropylamide in a solution of tetrahydrofuran/heptane/ethylbenzene (0.9 mL, 1.8 mmol) was added to a stirred solution of cis-[3-(3-hydroxypropenyl)phenoxy]acetic acid tert-butyl ester (421 mg, 1.56 mmol) in tetrahydrofuran (4.5 mL) at −78° C. under an argon atmosphere. The mixture was stirred for 10 minutes and solid diphenylcarbamoyl chloride (361 mg, 1.56 mmol) was added. The mixture was allowed to reach 0-5° C. and stirred for 16 hours. Saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate (9:1), gave cis-[3-(3-diphenylcarbamoyloxypropenyl)phenoxy]acetic acid tert-butyl ester (433 mg, 60.4%).

Provenance & Evidence