Reaktion #156131

Reaktionsgleichung

Water

Sodium hydride

5H-Furo[3,2-c]pyridin-4-one

Bromoacetaldehyde diethylacetal

→

title compound

5-(2,2-dihydroxyethyl)-5H-furo[3,2-c]pyridin-4-one

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 80° C. for 5 hours
2. 2
   Extraktionfollowed by extraction by ethyl acetate
3. 3
   TrocknenThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
4. 4
   workup.ADDITIONA 3N-hydrochrolic acid (5.8 ml) was added to an acetone solution (20 ml) of the residue
5. 5
   workup.STIRRINGthe liquid was stirred at 60° C. for 5 hours
6. 6
   workup.ADDITIONWater was added to the reaction liquid
7. 7
   workup.STIRRINGstirred at room temperature
8. 8
   SonstigeThe precipitated insoluble matter was separated
9. 9
   Waschenwashed with water
10. 10
    Sonstigedried

Vorschrift

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.

Quelle