Nitrogen → 1H-indol-4-ylmethanol

Participants

Reaction Steps

A solution of 25 g of methyl 4-indolecarboxylate (1) in 200 ml of tetrahydrofuran is added to a suspension of LiAlH4 in 100 ml of tetrahydrofuran under a protective-gas atmosphere (N2) at such a rate that the temperature of the reaction mixture does not exceed 40° C. When the addition is complete, the reaction mixture is stirred at room temperature (25° C.) for approximately two further hours until the methyl 4-indolecarboxylate has reacted completely. The reaction mixture is subsequently hydrolysed by addition of ice-water (about 100 ml), and the hydrolysate is filtered through a bed of kieselguhr. After the tetrahydrofuran has been removed by distillation, the aqueous phase obtained is extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulfate and evaporated, giving 16.0 g (76% of theory) of a pale-beige crystalline residue of 4-hydroxymethylindole (2).

Provenance & Evidence