Hydrogen Peroxide → 7-Ethenyl-1H-indole

To a 0° C. solution of 7-vinylindole 1 (0.95 g, 6.6 mmol) in anhydrous tetrahydrofuran (60 mL) was added 1 M borane-tetrahydrofuran complex in tetrahydrofuran (9.95 mL, 9.95 mmol) and the reaction stirred overnight at room temperature. 1 N sodium hydroxide (25 mL) and 30% hydrogen peroxide (35 mL) were then added and the mixture stirred at reflux for 1 hour. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water (50 mL) and saturated aqueous sodium chloride (2×50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 50% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 0.60 g (56%) of the desired compound as a yellow oil.

1. stirringthe mixture stirred
2. temperatureat reflux for 1 hour
3. temperatureThe reaction mixture was cooled to room temperature
4. washwashed with water (50 mL) and saturated aqueous sodium chloride (2×50 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. washeluting with 50% ethyl acetate in hexanes
8. additionFractions containing product
9. concentrationconcentrated under reduced pressure

ORD record

ord-68dc3925edd24866a62403914b204006

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867198B2