Triethylamine → Benzyl [hydroxy-(4-phenylbutyl)phosphinyl] acetate

Participants

Reaction Conditions

Reaction Steps

A solution of benzyl chloroformate (1.8 ml, 12.6 mmol) in 5 ml of dry tetrahydrofuran was added dropwise to a solution of [hydroxy(4-phenylbutyl)phosphinyl]acetic acid (2.55 g, 10 mmol) and triethylamine (2.0 ml, 14.5 mmol) in 30 ml of dry tetrahydrofuran at 0° C. After addition was complete, the mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. The mixture was positioned between ethyl acetate and 5% KHSO4 and the ethyl acetate layer was evaporated to a residue. The residue was taken up in aqueous NaHCO3, washed with ethyl acetate, and the aqueous solution acidified to pH 1 and extracted with ethyl acetate. The extracts were dried (Na2SO4) and evaporated to give the crude product which was triturated with pentane to yield a solid, melting point 64°-67° C. (3.30 g).

Provenance & Evidence