Sodium Hydroxide → (5-chloro-1H-indol-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Ethyl 5-chloro-2-indole-carboxylate (1 eq) was dissolved in THF (0.45M) under N2. This solution was cooled to 0° C. for fifteen minutes and then 1.1 eq LiAlH4 (1M in THF) was added. The resulting dark brown solution was allowed to return to rt with stirring and kept overnight. Then water (1/25 of the volume of the LiAlH4 solution) was added slowly, followed by 15% NaOH(aq) (1/25 of the volume of the LiAlH4 solution) solution. Finally, water (1/25 of the volume of the LiAlH4 solution) was added along with a large amount of MgSO4. Solution was filtered and the solid was washed with EtOAc and the filtrate was collected. Solvent was stripped off to give (5-chloro-1H-indol-2-yl)methanol (yellow solid) in 85% yield.

Provenance & Evidence