Sodium Hydroxide → HCID 4566228, compound

Participants

Reaction Steps

To a stirred solution of 5-methyl-2-phenyl-1H-indole (0.96 g, 0.00463 mol) in acetic acid (28.8 mL) was added sodium cyanoborohydride (0.873 g, 0.0139 mol) at RT and the resulting reaction mixture was stirred for 4 h. After completion of reaction (monitored by TLC), the reaction mixture was basified with sodium hydroxide solution and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx 0.5 inch) to provide the desired compound as a brown colored oil (0.7 g, 72% yield).

Provenance & Evidence