反应详情

温度

-50 °C

Diisobutylaluminum hydride (1M in toluene, 12 mL, 12 mmol) was added to a solution of 1-tert-butyl 6-methyl 1H-indole-1,6-dicarboxylate (1.38 g, 5.00 mmol) in toluene (15 mL) at −50° C. over 10 minutes. After being stirred at −50° C. for 30 minutes, the reaction was quenched with methanol (2.5 mL) and water (2.5 mL). The resulting precipitate was filtered off, and the filtrate was evaporated. The residue was purified by silica gel chromatography, eluting with petroleum ether/ethyl acetate (5:1 to 1:1) to afford tert-butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate (815 mg, 55% yield) as an oil. LCMS (ESI) m/z 174.3 [M+H-18-56]+, 230.3 [M+H-18]+.

1. customthe reaction was quenched with methanol (2.5 mL) and water (2.5 mL)
2. filtrationThe resulting precipitate was filtered off
3. customthe filtrate was evaporated
4. customThe residue was purified by silica gel chromatography
5. washeluting with petroleum ether/ethyl acetate (5:1 to 1:1)