Triethylamine → Methyl (3E)-4-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)but-3-enoate

Participants

Reaction Steps

Under an argon atmosphere, a mixture of (2R)-2-{[(1R)-1-(2-bromophenyl)ethoxy]methyl}oxirane (1.00 g, 3.89 mmol) described in WO 2004/094362, methyl but-3-enoate (497 μL, 4.67 mmol), palladium acetate (II) (44 mg, 0.19 mmol), tris(2-methylphenyl)phosphine (59 mg, 0.19 mmol), and triethylamine (0.65 mL, 4.67 mmol) in acetonitrile (10 mL) was stirred with heating under reflux for 3 hours. The reaction solution was cooled to room temperature, filtered through Celite, and washed with acetonitrile. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a yellow oily substance (246 mg, yield 23%).

Provenance & Evidence