Dichloromethane → HCID 22563213, compound

Participants

Reaction Steps

To a solution of ethyl 2-formyl-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (1.0 g, 3.8 mmol) in 1,2-dichloroethane (23 mL) was added sodium triacetoxyborohydride (1.6 g, 7.5 mmol). The reaction was stirred at room temperature for 24 hours. The reaction was poured into sat. aq. sodium bicarbonate (50 mL) and methylene chloride (30 mL), before it was quenched with water (50 mL). The mixture was allowed to stand at 0° C. overnight. The solid ppt. was collected by vacuum filtration and washed with water. Drying in vacuo yielded an off-white solid (0.36 g, 36%). The filtrate was concentrated to near dryness and diluted with water (20 mL). Filtration followed by treatment with high vacuum gave a second crop of product (0.45 g).

Provenance & Evidence