Dichloromethane → HCID 57672411, compound

Participants

Reaction Steps

To a stirred solution of (S,E)-ethyl 3-(4-methoxy-2-methylphenyl)hex-4-enoate 28.6 (0.500 g, 2 mmol) in DCM (19 mL, 2 mmol) at 0° C. was added boron tribromide (9 mL, 9 mmol). The resulting mixture was stirred for 1 hour. The reaction wasquenched by the addition of pH 7 buffer. The resulting mixture was extracted with DCM. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford (S,E)-ethyl 3-(4-hydroxy-2-methylphenyl)hex-4-enoate (28.7) (0.12 g, 25% yield) as a colorless oil. MS ESI (pos.) m/e: 266.2 (M+H2O), 249.1 (M+H).

Provenance & Evidence