反应详情

温度

0 °C

1-benzyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.0 g, 15.9 mmol) was dissolved in THF (75 mL) and cooled to −78° C. n-Butyl lithium (2.5 M in hexane, 7.0 mL, 17.5 mmol) was added dropwise and the mixture was warmed to 0° C. over 15 minutes. Cooled to −78° C. and (2-Bromoethoxy)-tert-butyldimethylsilane (5.2 mL, 23.9 mmol) was added and the mixture was allowed to warm to 25° C. The mixture was stirred for 2 hours then quenched with saturated aqueous ammonium chloride, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 0-10% ethyl acetate in hexane) to afford 4.1 g (63%) 1-(3-{[tert-butyl)dimethyl)silyl]oxy}-1-phenylpropyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one.

1. additionwas added dropwise
2. temperatureCooled to −78° C.
3. temperatureto warm to 25° C
4. customthen quenched with saturated aqueous ammonium chloride
5. additiondiluted with ether
6. washwashed with water, and saturated brine
7. customThe organic layer was separated
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 0-10% ethyl acetate in hexane)