p-Toluenesulfonic acid → HCID 21898047, compound

Participants

Reaction Conditions

Reaction Steps

A solution of thiophene (0.60 mL, 7.5 mmol) in THF (15 mL) was cooled to −78° C., BuLi solution (2.5 M in hexanes, 3.0 mL, 7.5 mmol) was added dropwise, after 1 h at −78° C., a solution of 1-(4-hydroxy-phenyl)-ethanone (1.0 g, 7.34 mmol) was added. The slurry mixture was stirred at −78° C. for 2 h, then slowly warmed to rt. The reaction was quenched with saturated aqueous NH4Cl, extracted with ethyl acetate, the extract was washed with brine, dried over MgSO4 and concentrated to give yellow oil residue. To the above oil residue was added benzene (10 mL) and catalytic amount of TsOH. The mixture was heated with Dean-Stark trap for 15 min, then concentrated 4-(1-Thiophen-2-yl-vinyl)-phenol (170 mg, 11.5%) was obtained after flash column chromatography (20%–40% ethyl acetate-hexanes). MS Found: (M+H)+=203.

Provenance & Evidence