Ethanol → Ethyl 2-(tert-butoxy)-2-(3,5-diphenylthiophen-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate (100 mg, 0.25 mmol), phenylboronic acid (36 mg, 0.30 mmol) and sodium carbonate (106 mg, 1.00 mmol) in a mixture of toluene (1.26 mL), ethanol (0.6 mL) and water (0.5 mL) was bubbled with nitrogen for 5 minutes. Palladium tetrakis(triphenylphosphine) (14 mg, 0.01 mmol) was added and the reaction mixture was heated a 95° C. overnight. After cooling to room temperature, water (2 mL) was added. The aqueous layer was extracted with toluene (2×8 mL). The organic layers were washed with brine (5 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to provide ethyl 2-(tert-butoxy)-2-(3,5-diphenylthiophen-2-yl)acetate (50 mg, 0.13 mmol, 51%).

Provenance & Evidence