Boron trifluoride → 1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

Participants

Reaction Steps

To a solution of 2,3-di(4-benzyloxy-phenyl)-1,3-butadiene (1.2 g, 2.8 mmol) and 2-methyl-propenal (0.602 g, 8.4 mmol) in DCM (10.5 mL) was added BF3.OCH2CH3 (0.596 mL, 4.2 mmol) at −10° C. After 3 h at −10° C., the reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL). The reaction mixture was then extracted with ethyl acetate (2 10 mL), dried over MgSO4 and purified by SiO2 twice (15% ethyl acetate/hexane) to yield 1-methyl-3,4-di(4-benzyloxy-phenyl )-cyclohex-3-ene carbaldehyde.

Provenance & Evidence