Dimethylformamide → Ethyl (+/-)-10,11-dihydro-2-formyl-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Participants

Reaction Conditions

Reaction Steps

POCl3 (17 mL) was added dropwise to a solution of ethyl (±)-10,11-dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate (1.0 g, 3 mmol) in dry DMF (40 mL) at RT under argon, and the dark solution was heated at 90° C. for 48 hr. The reaction was concentrated on the rotavap and the residue was partitioned between H2O and EtOAc. The organic layer was separated, dried (MgSO4), and concentrated on the rotavap. The residue was reconcentrated from xylenes (to remove any remaining DMF) then was chromatographed on silica gel (7% EtOAc in hexanes) to afford the title compound (230 mg, 21%) as a colorless oil: MS (ES) m/e 339.3 (M+H)+.

Provenance & Evidence