Sodium bis(trimethylsilyl)amide → 6-Bromo-3,3-dimethyl-1-(2-trimethylsilylethoxymethyl)indolin-2-one

Participants

Reaction Steps

A solution of 6-bromo-3,3-dimethylindolin-2-one (example 14a, 4.87 g, 20.3 mmol) in THF (135 ml) was cooled to 0° C. and a solution of sodium bis(trimethylsilyl)amide in THF (1M, 24.3 ml, 24.3 mmol) was added during 15 minutes. Then a solution of (2-(chloromethoxy)ethyl)trimethylsilane (4.27 g, 4.54 ml, 24.3 mmol) in THF (5 ml) was added during 15 minutes. After 4 hours at 0° C. the reaction mixture was poured into ice-water.

Provenance & Evidence