Sodium Hydroxide → HCID 19921640, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-acetyl-3-[3-(t-butyldimethylsiloxy)propyl]-2-trimethylsily 1-1H-indole (1.8 g, 5 mmol) in acetonitrile (100 mL) was added a 50% HF solution (4 mL) After stirring for 24 h at 23° C., the reaction was made basic (pH 10) by the addition of 50% NaOH solution and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated NaCl and next with water. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (CH2Cl2 :MeOH:NH4OH; 95:5:0.5) of the concentrate afforded 1-[5-acetyl1H-indol-3-yl]-3-propanol (0.91 g, 94%).

Provenance & Evidence