Ammonium Chloride → HCID 53995625, compound

Participants

Reaction Steps

2.0 M Lithium diisopropylamide in toluene/heptane/ethylbenzene (0.77 mL, 1.54 mmol) was added to a stirred solution of [3-(3-hydroxyprop-1-ynyl)-2-methylphenoxy]acetic acid tert-butyl ester (370 mg, 1.34 mmol) in tetrahydrofuran (4 mL) at −78° C. under an argon atmosphere. The mixture was stirred for 10 minutes and solid diphenylcarbamyl chloride (310 mg, 1.34 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 washed with brine, dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave [3-(3-diphenylcarbamoyloxyprop-1-ynyl)-2-methylphenoxy]acetic acid tert-butyl ester as a colorless oil (220 mg, 35%).

Provenance & Evidence