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

Participants

Reaction Steps

A mixture of ethyl 2-hydroxy-2-(3-phenyl-1-benzothiophen-2-yl)acetate (3b) (340 mg, 1.09 mmol), silver (I) oxide (758 mg, 3.27 mmol) and tertbutylbromide (612 μL, 5.45 mmol) in cyclohexane (20 mL) was vigorously stirred for 48 hours under a nitrogen atmosphere. 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 (3c) as a white solid (45 mg, 0.12 mmol, 11%).

Provenance & Evidence