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

HRID 1504121Notes

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-hydrochloric 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-hydrochloric 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-5073cab6a6fc46a7820ca86b0a451ea5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212187B2

Reaction notes

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