Sodium Hydroxide → (6-Phenylthio-2-pyridyl)methanol

Participants

Reaction Steps

To a cooled solution of 6-phenylthio-2-pyridylcarboxylic acid (0.75 g, 3.25 mmol) in 10 ml of tetrahydrofuran in an ice bath is added dropwise a borane-tetrahydrofuran solution (6.7 ml total, 6.70 mmol) over a period of 20 minutes. The reaction mixture is stirred at RT overnight. 3 N aqueous sodium hydroxide (4 ml) is added slowly and stirring is continued for another 8 hours. The solution is diluted with water, saturated with solid potassium carbonate and extracted with water. The extract is washed with water, saturated NaHCO3 and brine and dried to yield (6-phenylthio-2-pyridyl)methanol.

Provenance & Evidence