Ethyl Acetate → (E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate

Participants

Reaction Steps

To a solution of (carbethoxyethylidene)triphenylphosphorane (5.50 g, 15.2 mmol) (commercially available from Aldrich, catalog #377708) in THF (25 mL) was added 4-(benzyloxy)benzaldehyde (12.1) (2.93 g, 13.8 mmol) (commercially available from Lancaster, catalog #6285) in THF (10 mL) under nitrogen at −78° C. The reaction was allowed to slowly warm to room temperature and stirred for 2 hours. EtOAc (100 mL) was added, and the mixture was washed with brine (30×2 mL). The organic layer was dried over MgSO4. The solvent was removed by evaporation. The crude product was purified by passing through a short silica gel column, eluting with hexane/EtOAc (85/15) to give the title compound. 1H NMR (CDCl3) δ 7.65 (s, 1H), 7.46-7.35 (m, 7H), 7.01 (d, 2H), 5.11(s, 2H), 4.28 (q, 2H), 2.14 (s, 3H), 1.36 (t, 3H).

Provenance & Evidence