1-Chloro-4-(chloromethyl)benzene → 3-(4-Chlorobenzyloxy)-1-(diphenylmethyl) azetidine

Participants

Reaction Steps

A solution of 1-diphenylmethyl-3-azetidinol (25 mmol) in DMF (100 mL) was added at 0° C. to a suspension of NaH (60% disp.in oil, 30 mmol) in DMF (50 mL). The reaction mixture was stirred at room temperature for 1 h, then 4-chlorobenzylchloride (25 mmol) was added dropwise at 0° C. and the reaction mixture stirred at room temperature for 3 h. The reaction was quenched with water and extracted with ethyl acetate (3×50 mL), the extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography [SiO2; hexane-ethyl acetate (9:1)] to yield the product as a yellow oil (7.3 g, 80%). The material was used in the next step without further purification.

Provenance & Evidence