Water → HCID 68841498, compound

Participants

Reaction Conditions

Reaction Steps

2-(2-(triethylsilyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanol (1.99 g, 7.24 mmole) was dissolved in THF (17 ml) and TBAF (7.96 ml, 7.96 mmole; 1 M solution in THF) was added at 0° C. The mixture was stirred for 1 hour at 0° C. and then heated to RT. Further TBAF (7.96 ml, 7.96 mmole, 1 M solution in THF) and H2O (5 drops) were added. After 2 days at RT 20 ml of H2O were added and the aqueous phase was extracted with DCM (3×60 ml). The organic phases were combined and washed with saturated NaCl solution (2×20 ml) and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator and the residue was purified by column chromatography (DCM/MeOH=4:1). 2-(1H-pyrrolo[2,3-c]pyridin-3-yl)ethanol (0.60 g, 51%) was formed as a colourless oil, which solidified over time.

Provenance & Evidence