Water → 5-(2,2-Dihydroxyethyl)-5h-furo[3,2-c]pyridin-4-one

HRID 68949Notes

Reaction equation

[H-].[Na+].[O:3]1[C:11]2[CH:10]=[CH:9][NH:8][C:7](=[O:12])[C:6]=2[CH:5]=[CH:4]1.C([O:15][CH:16]([O:19]CC)[CH2:17]Br)C.O>CN(C=O)C>[OH:15][CH:16]([OH:19])[CH2:17][N:8]1[CH:9]=[CH:10][C:11]2[O:3][CH:4]=[CH:5][C:6]=2[C:7]1=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% in oil, 0.36 g) was suspended in DMF (10 ml), and was cooled to 0° C. in an ice water bath. 5H-Furo[3,2-c]pyridin-4-one (1.0 g) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. Bromoacetaldehyde diethylacetal (2.6 ml) was added thereto, and the mixture was stirred at 80° C. for 5 hours. Water was added to the reaction liquid, followed by extraction by ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. A 3N-hydrochrolic acid (5.8 ml) was added to an acetone solution (20 ml) of the residue, and the liquid was stirred at 60° C. for 5 hours. Water was added to the reaction liquid and stirred at room temperature. The precipitated insoluble matter was separated, washed with water, and dried to give the title compound (0.90 g) as a white solid.

Workup

stirringthe mixture was stirred at 80° C. for 5 hours
extractionfollowed by extraction by ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
additionA 3N-hydrochrolic acid (5.8 ml) was added to an acetone solution (20 ml) of the residue
stirringthe liquid was stirred at 60° C. for 5 hours
additionWater was added to the reaction liquid
stirringstirred at room temperature
customThe precipitated insoluble matter was separated
washwashed with water
customdried

Sources & evidence

ORD record: ord-f963c59e248a490eb8911690ec354794
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Reaction notes

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