Acetic Acid → 1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanol

Participants

Reaction Steps

1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl}ethanone (96.89 g, 479 mmol) in methanol (1000 mL) was cooled in an ice/water bath. Sodium borohydride (29 g, 767 mmol) was added over 1 hour 30 minutes. After stirring for 40 minutes aq. acetic acid (70%, 20 mL) was added and the mixture was concentrated. Dichloromethane (400 mL) was added to the residue and was extracted with saturated aqueous sodium hydrogen carbonate (500 mL). The aqueous layer was extracted with dichloromethane (170 mL), and the combined organic layer was washed with aqueous hydrochloric acid (0.5 M, 250 mL), followed by aqueous hydrogen carbonate (280 mL), then washed with brine (500 mL), dried over sodium sulfate, filtered and concentrated to give the title product (95 g, 97%).

Provenance & Evidence