t-Butyl bromide → ethyl 2-(tert-butoxy)-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate

Participants

Reaction Steps

A mixture of ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate (1c) (300 mg, 0.97 mmol), silver (I) oxide (674 mg, 2.91 mmol) and tert-butylbromide (544 μL, 4.85 mmol) in cyclohexane (10 mL) was vigorously stirred for 2 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 (1d) as a white solid (35 mg, 0.1 mmol, 10%).

Provenance & Evidence