Tetrahydrofuran → 5,6-dichloro-1H-indole-2-carbaldehyde

ethyl 3-(5,6-dichloro-2indolyl)-2-propenoate (16.23 g, 57.1 mmol) was dissolved under nitrogen in dry THF (300 ml) cooled at -20° and 1M DIBAL in hexanes (115 ml, 115 ml) was added dropwise at -20° C. The reaction mixture was maintained at this temperature for 1 hour and then quenched with H2O. The mixture was warmed to RT, diluted with Et2O (200 ml) and filtered on a Celite pad, washing with 300 ml of Et2O. The dark-red solution was dried over MgSO4 and evaporated under vacuum to give pure title compound (13.8 g, 57.0 mmol, yield 99.8%).

1. temperaturecooled at -20°
2. temperatureThe reaction mixture was maintained at this temperature for 1 hour
3. customquenched with H2O
4. additiondiluted with Et2O (200 ml)
5. filtrationfiltered on a Celite pad
6. washwashing with 300 ml of Et2O
7. dry with materialThe dark-red solution was dried over MgSO4
8. customevaporated under vacuum

ORD record

ord-8b7bcb129d8247db8ec10b7b79fd59d0

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05985905