Methanol → 1-[4-(Benzyloxy)phenyl]-4,4,4-trifluorobutane-1,3-dione

Participants

Reaction Steps

A solution of 4-benzyloxyacetophenone (6.50 g, 29 mmol) in ether (70 mL) was cooled to 0° C. and treated with ethyl trifluoroacetate (4.12 g, 29 mmol) and 25% sodium methoxide in methanol (6.39 g, 30 mmol). The reaction was warmed to room temperature and stirred for 64.4 hours. The reaction was quenched with 3 N HCl (15 mL), extracted with ethyl acetate, washed with brine, dried over anhyd. MgSO4, filtered and concentrated in vacuo to give the title compound as a yellow solid (8.91 g, 96%): mp 92.4-96.5° C. 1H NMR (CDCl3) 15.30 (br s, 1 H), 8.86 (d, 2 H, J=8.9 Hz), 7.43 (m, 5 H), 7.08 (d, 2 H, J=8.9 Hz), 6.50 (s, 1 H) 5.16 (s, 2 H).

Provenance & Evidence