(6-Chloro-1H-indol-2-yl)-methanol

27034-51-1

53590-58-2

General procedure for the synthesis of 2-hydroxymethyl-6-chloroindole from ethyl 6-chloroindole-2-carboxylate: 2.00 g (8.94 mmol) of ethyl 6-chloroindole-2-carboxylate was dissolved in 50 ml of ethyl ether at 0°C, and 0.475 g (12.5 mmol) of lithium aluminum hydride was added slowly. The reaction mixture was heated to 45°C to reflux the reaction. Upon completion of the reaction, 10 ml of water, 10 ml of 2M aqueous sodium hydroxide solution and 10 ml of water were added sequentially at 0°C to quench the reaction. The aqueous layer was separated and extracted with tert-butyl methyl ether (3 x 100 ml). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product 2-hydroxymethyl-6-chloroindole (1.64 g; 100% yield) as a white solid. MS data: MS m/e (relative abundance): 180 ([M-H]+, 100).