Hydrochloric Acid → [4-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester

Beteiligte Stoffe

Reaktionsschritte

A dispersion of sodium hydride in mineral oil (55%, 61 mg, 1.4 mmol) was added to a solution of 4-(tert-butyl-dimethyl-silanyloxy)-1H-indole [251 mg, 1 mmol; Eur. Pat. Appl. (1986), EP 206225 A2] and bromo-acetic acid tert-butyl ester (160 μl. 1, 1.1 mmol) in N,N-dimethylformamide (10 ml) at 0° C. under an argon atmosphere. The reaction mixture was naturally warmed to ambient temperature, stirred for 14 h and cooled to 0° C. Ice water (10 ml) and concentrated HCl (2 ml) were added and the mixture was extracted three times with dichloromethane. The combined extracts were washed with brine and water and dried over sodium sulfate. The solvent was removed under reduced pressure to give a yellow liquid which was purified by column chromatography (silica gel, heptane/AcOEt) to give 246 mg (0.68 mmol, 67%) of the title compound as light yellow oil.

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