Triethyl orthoacetate → HCID 57672468, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S,E)-4-(4-methoxy-2-methylphenyl)but-3-en-2-ol 28.5 (2.00 g, 10 mmol) (99% ee) in triethyl orthoacetate (20 mL, 109 mmol) at 23° C. was added propanoic acid (0.01 mL, 0.1 mmol). The reaction mixture was heated to 155° C., and stirred for 24 hours. The reaction was cooled to room temperature and concentrated in vacuo. The resulting product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound (S,E)-ethyl 3-(4-methoxy-2-methylphenyl)hex-4-enoate 28.6 (1.22 g, 45% yield) as a clear oil. MS ESI (pos.) m/e: 280.1 (M+H2O), 263.1 (M+H).

Provenance & Evidence