Sodium Bicarbonate → Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate

Participants

Reaction Conditions

Reaction Steps

47.43 ml (47.73 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 8 g (23.71 mmol) of methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate in 200 ml of THF at −10° C. After warming to −5° C., the mixture is stirred at this temperature for a further 4 hours. After reaction is complete, the reaction mixture is mixed with saturated sodium bicarbonate solution, and the solvent is concentrated to dryness. The residue is taken up in dichloromethane, dried over sodium sulfate and again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10). 5.8 g (98% purity, 74% of theory) of a colorless solid are obtained.

Provenance & Evidence