Acetic Acid → Ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 0° C. mixture of ethyl 2-formyl-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (695 mg, 2.49 mmol) and glacial acetic acid (0.71 mL, 12.5 mmol) in 1,2-dichloroethane (23 mL) was added sodium triacetoxyborohydride (1.06 g, 4.98 mmol). After stirring for 5 min at 0° C., the reaction was stirred at room temperature for 3.5 hours. The reaction was poured into sat. aqueous. sodium bicarbonate (50 mL) and methylene chloride (30 mL), stirred vigorously for 5 minutes, and filtered. The collected solid was washed with water and methylene chloride, then dried in vacuo, leaving an off-white solid (665 mg, 93%).

Provenance & Evidence