Tetrahydrofuran → HCID 86583978, compound

Participants

Reaction Steps

To a solution of 1,3-dichloro-phenyl acetylene (6.07 g, 35.5 mmol) in dry THF (60 mL) was added palladium acetate (186 mg, 0.68 mmol), ethyl 2-butynoate (5.97 g, 53.2 mmol) and tris (2,6-dimethoxyphenyl)phosphine (316 mg, 0.68 mmol) at room temperature. The reaction mixture was stirred for 18 h and filtered. The filtrate was washed with water (10 mL), and the water phase was extracted with ether (10 mL). The combined organic phases were dried and evaporated. The residue was purified by column chromatography using heptane:THF (20:1) as eluent. (E)-3-Methyl-5-(3,5-dichloro-phenyl)-pent-2-en-4-ynoic acid ethyl ester was isolated in 4.65 g (46%) yield.

Provenance & Evidence