1-(Diphenylmethyl)azetidin-3-one → 1-Benzhydryl-3-(4-chloro-phenyl)-azetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-chlorophenylmagnesium bromide (9.1 mL, 10 M in diethyl ether) in diethyl ether (80 mL) at −78° C. under an argon atmosphere was added compound 3 (1.8 g, 7.6 mmol) in diethyl ether (50 mL) dropwise over 20 minutes. The reaction mixture was stirred at −78° C. for 2 hours, then slowly warmed to room temperature with stirring over 18 hours. The reaction mixture was then partitioned between aqueous ammonium acetate solution (50 mL) and diethyl ether (50 mL). The aqueous layer was extracted with diethyl ether (3×50 mL) and the combined organic extracts were washed (water, brine), dried (Na2SO4), filtered and concentrated in vacuo to give the crude product as a pale yellow viscous oil in quantitative yield. A sample purified for analysis by column chromatography on silica gel using 15-30% ethyl acetate-hexane as eluent and subsequent crystallisation from bexane gave 3-(4-chorophenyl)-1-(diphenyhnethyl)-3-azetidinol (4), m.p. 108° C. Found: C, 75.42; H, 5.79; N, 3.98. C22H20CINO requires C, 75.53; H, 5.76; N, 4.00%.

Provenance & Evidence