HCID 13720819, compound → HCID 14882500, compound

Participants

Reaction Steps

A solution of methyl 1-(4-methylphenylsulfonyl)indole-6-carboxylate (28.0 g) in tetrahydrofuran (250 ml) was added dropwise to a slurry of lithium aluminum hydride (4.5 g) in tetrahydrofuran (300 ml) at 0°. After stirring at 0° for 15 minutes, the excess lithium aluminum hydride was quenched with a saturated solution of sodium sulfate and the resultant white precipitate was removed by filtration. The filtrate was dried (MgSO4) and evaporated to give 6-hydroxymethyl-1-(4-methylphenylsulfonyl)indole (21.5 g, 84%) as an ivory solid; partial NMR (80 MHz, CDCl3): 2.33(s, 3H, ArCH3), 4.77(d, 2H, OCH2), 6.62(dd, 1H, H3 -indole), 7.97(m, 1H, H7 -indole).

Provenance & Evidence