t-Butyl bromide → Ethyl 2-(tert-butoxy)-2-(2-phenyl-1-benzothiophen-3-yl)acetate

Participants

Reaction Steps

A mixture of ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate (2c) (190 mg, 0.6 mmol), silver (I) oxide (417 mg, 1.8 mmol) and tertbutylbromide (360 μL, 3.2 mmol) in cyclohexane (5 mL) was vigorously stirred for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (2d) as a white solid (30 mg, 0.08 mmol, 13%).

Provenance & Evidence