Isopropanol → 2-Chloro-N-[3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]acetamide

Participants

Reaction Conditions

Reaction Steps

(2RS,3RS)-1,2-Epoxy-3-(2-ethoxyphenoxy)-3-phenylpropane (47.7 g) and dimethyl carbonate (700 mL) were stirred to form a white slurry. Triethylamine (52 mL) was added and the mixture cooled to 6-10° C. using an ice/H2O bath, a solution of chloroacetyl chloride (13.8 mL) in dimethyl carbonate (50 mL) was added over a 30 minute period keeping the temperature between 4-10° C. The mixture was stirred for 1 hour. The mixture was washed with 500 mL of H2O and then with 500 mL of 3% aqueous NaCl solution. The organic layer was concentrated under vacuum at 40° C. to yield a dark oil. Isopropanol (500 mL) was added and the mixture again concentrated to remove any residual dimethyl carbonate, yielding the title compound.

Provenance & Evidence