1-Chloroethyl chloroformate → Ethyl acetate methanol ammonium hydroxide

Participants

Reaction Steps

To a stirred solution of 1-benzhydryl-3-(2,4,4′-trichlorobenzhydryloxy)azetidine (3) (39 mmol) in dichloromethane (400 mL) was added 1-chloroethylchloroformate (98 mmol) dropwise at 0° C. and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, then dissolved in methanol (400 mL) and stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo, then diluted with ethyl acetate (400 mL) and washed with sodium hydroxide (5N, 400 mL), dried (MgSO4) and concentrated in vacuo to furnish a yellow oil. The residue was purified by filtration through silica, eluting with dichloromethane, then [ethyl acetate:methanol:ammonium hydroxide (90:8:2)] to yield a yellow oil (8.0 g, 60%).

Provenance & Evidence