Diisobutylaluminumhydride → HCID 22262935, compound

Participants

Reaction Conditions

Reaction Steps

Diisobutylaluminum hydride (6 ml, 6 mmol, 1M in dichloromethane) was added slowly at −78° C. under N2 to a solution of 1-methanesulfonyl-5-methoxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester (0.4 g, 1.29 mmol) in anhydrous tetrahydrofuran (10 ml). The reaction mixture was stirred at −78° C. for 1.5 hours and then kept at 4° C. for 16 hours. The reaction was quenched with water and stirred for 0.5 hour. The insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography over silica gel eluting with 50 to 70% ethyl acetate in hexane to give (1-methanesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)-methanol as a white solid, (0.26 g, 75.2%). 1H NMR (CDCl3) δ: 2.59 (s, 3H), 3.00 (s, 3H), 3.87 (s, 3H), 4.79 (bs, 2H), 6.91 (dd, 1H, J=9.1 Hz, 2.6 Hz), 7.11 (d, 1H, J=2.6 Hz), 7.89 (dd, 1H, J=9.1 Hz, 0.3 Hz).

Provenance & Evidence