3-(4-Benzyloxy-phenyl)-N-methoxy-N-methyl-propionamide → 1-(4-Benzyloxyphenyl)-heptan-3-one

Participants

Reaction Steps

The title compound was prepared by treating 3-(4-benzyloxy-phenyl)-N-methoxy-N-methyl-propionamide prepared in Example T (8.5 g, 28 mmol) with n-butyl magnesium chloride (21.4 mL, 2.0M, 42.8 mmol) in 100 mL of THF. The reaction mixture was stirred at room temperature for 1 hour and refluxed for 3 hours. The reaction mixture was cooled to 0° C., quenched with 1N HCl, and extracted with EtOAc. After evaporation of the solvents, the crude product was purified by flash silica gel column chromatography, eluting with EtOAc:hexane (5:95, then switching to 3:7). 1H NMR (CDCl3) δ 0.86 (t, 3 H), 1.27 (m, 2 H), 1.34 (m, 2 H), 2.33 (t, 2 H), 2.64 (t, 2 H), 2.78 (t, 2 H), 5.0 (s, 2 H), 6.85 (d, 2 H), 7.06 (d, 2 H), 7.25 (t, 1 H), 7.31-7.42 (m, 4 H).

Provenance & Evidence