Diisobutylaluminum hydride → [3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (3.24 g, 7.72 mmol) in toluene (40 mL) cooled to −78° C. and under a nitrogen atmosphere was added 1.0M DIBAL-H in toluene (23.2 mL, 23.2 mmol). The reaction mixture was stirred at −78° C. for 15 min and then at −10° C. for 30 min. After re-cooling to −78° C., the reaction mixture was quenched with water (20 mL) and then allowed to warm to RT. The mixture was partitioned between EtOAc and 1.0M HCl and the aqueous phase was extracted with additional EtOAc (×3). The combined organic layers were washed with water, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane) affording [3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol as a white foam (2.49 g, 85%). LCMS: RT 4.77 min [M+Na]+ 400.1.

Provenance & Evidence