Ammonium Chloride → 1497198-86-3

Participants

Reaction Steps

To a solution of tert-butyl 3-oxoazetidine-1-carboxylate (4 g, 23 mmol) in THF (100 mL) at 0° C. was added (4-methoxyphenyl)magnesium bromide (0.5 M in ether) (47 mL, 23 mmol). The reaction mixture was stirred for 3 h, and then a satd. ammonium chloride solution (200 mL) was added. The mixture was extracted with ethyl acetate (200 mL), and the organic layer was separated, dried over Na2SO4, and evaporated under reduced pressure to give a crude product. The product was purified by silica gel chromatography eluting with 25% ethyl acetate in hexane to give tert-butyl 3-hydroxy-3-(4-methoxyphenyl)azetidine-1-carboxylate (2.2 g, 7.64 mmol, 32.7% yield). LCMS (Method 107): m/z 280.7 (M+H) RT=1.929 min; 1H NMR (400 MHz, DMSO-d6) δ 7.39 (d, J=8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 6.21 (s, 1H), 4.00 (s, 3H), 3.75 (s, 3H), 1.41 (s, 9H).

Provenance & Evidence