Ethyl Acetate → HCID 68690094, compound

Participants

Reaction Steps

To a solution of methyltriphenylphosphonium bromide (714 mg, 2 mmol) in ether at 0° C. was added dropwise 1.6 M n-BuLi solution in hexane (1.25 mL, 2.00 mmol). The resultant solution was stirred at 0° C. for 40 min and then was warmed to room temperature. A solution of 2-formyl-3,4-dimethylthiophene trimer (432 mg, 1.2 mol) was added slowly and the mixture was stirred overnight. The reaction mixture was quenched with ammonium chloride solution and diluted with ether. The organic phase was washed with water and brine, and dried with MgSO4. The ether was removed in vacuo to afford the crude product as an oil (260 mg). Column chromatography (2% EtOAc in hexane) afforded the purified 2-vinyl-3,4-dimethylthiophene trimer (140 mg, 37% yield). EI-MS: 358 (M+). 1H NMR (CDCl3) δ 6.98 (s, 1H), 6.90 (dd, 1H), 5.52 (d, 1H), 1.15 (d, 1H), 2.22 (s, 1H), 2.19 (s, 1H), 2.11 (s, 1H), 2.10 (s, 1H), 2.09 (s, 1H), 2.08 (s, 1H).

Provenance & Evidence