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

HRID 23616Notes

Reaction equation

[CH:1]([C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]([CH3:18])[C:5]=2[C:4]=1[CH3:19])=[O:2].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(Cl)Cl>[OH:2][CH2:1][C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]([CH3:18])[C:5]=2[C:4]=1[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

stirringthe reaction was stirred at room temperature for 3.5 hours
additionThe reaction was poured into sat. aqueous
filtrationfiltered
washThe collected solid was washed with water and methylene chloride
customdried in vacuo

Sources & evidence

ORD record: ord-7f524fd095b3462283c893d5c738a549
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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