Water → (RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanol

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Reaction Steps

(RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester (2.5 g, 12.06 mmol) in THF (130 ml) was added dropwise to a suspension of LiAlH4 in THF (80 ml) at 4° C., and the mixture allowed to stir at RT overnight, and then heated at 65° C. for 4 hr. After cooling, H2O (20 ml) was added cautiously and the mixture stirred 20 min, then filtered and the filtrate extracted with EtOAc (3×50 ml), the extracts were washed with satd. NaCl solution (50 ml), dried (Na2SO4) filtered and evaporated. The crude oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (9:1) affording (RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanol as a yellow oil (1.41 g, 7.86 mmol, 65%), MS: m/e=179.1 (M+).

Provenance & Evidence