Ethyl Acetate → HCID 12467033, compound

Participants

Reaction Steps

To the suspension of lithium aluminum hydride (4.15 g) in tetrahydrofuran (41 ml) at 15°-30° C. under a nitrogen atmosphere was added dropwise over 45 minutes 3-ethyl-2-indolecarboxylic acid methyl ester [22.2 g) in tetrahydrofuran. After the mixture was stirred at room temperature for an hour, ethyl acetate (200 ml) was added dropwise at 20°-30° C., followed by the addition of methanol (10 ml) at the same temperature. The reaction mixture was treated with saturated aqueous potassium sodium tartrate solution (150 ml). Separated organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (10% ethylacetate-n-hexane) to give 3-ethyl-2-hydroxymethylindole (14.0 g) as crystals.

Provenance & Evidence