Reaktion #2477095

Reaktionsgleichung

dimethyl 3-hydroxy-5-(3-methoxy-3-oxopropyl)furo[2,3-c]pyridine-2,4-dicarboxylate

hydrochloric acid

trimethylsilyldiazomethane diethyl ether

→

title compound

Ausbeute 81.2%

methyl 5-(3-methoxy-3-oxopropyl)-2,3-dihydrofuro[2,3-c]pyridine-4-carboxylate

Ausbeute 81.2%

Lösungsmittel

sodium hydrogen carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (60 mL)
3. 3
   workup.ADDITIONpalladium-carbon powder (600 mg) was added
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere
5. 5
   FiltrationThe catalyst was filtered off
6. 6
   Sonstigethe filtrate was evaporated under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue was dissolved in methanol (60 mL) again
8. 8
   workup.ADDITIONpalladium-carbon powder (1.00 g) was added
9. 9
   workup.STIRRINGthe mixture was stirred at 50° C. for 4 hr under a hydrogen atmosphere
10. 10
    FiltrationThe catalyst was filtered off
11. 11
    Sonstigethe filtrate was evaporated under reduced pressure
12. 12
    workup.DISSOLUTIONThe residue was dissolved in methanol (60 mL)
13. 13
    Temperaturcooling
14. 14
    workup.STIRRINGthe mixture was stirred for 30 min
15. 15
    Extraktionthe mixture was extracted with ethyl acetate
16. 16
    TrocknenThe extract was dried over anhydrous sodium sulfate
17. 17
    Sonstigethe solvent was evaporated under reduced pressure

Vorschrift

A mixture of dimethyl 3-hydroxy-5-(3-methoxy-3-oxopropyl)furo[2,3-c]pyridine-2,4-dicarboxylate (3.10 g, 9.19 mmol) and 12M hydrochloric acid (31 mL) was stirred at 150° C. for 1 hr and concentrated under reduced pressure. The residue was dissolved in methanol (60 mL), palladium-carbon powder (600 mg) was added, and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was dissolved in methanol (60 mL) again, palladium-carbon powder (1.00 g) was added, and the mixture was stirred at 50° C. for 4 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was dissolved in methanol (60 mL), 2M trimethylsilyldiazomethane/diethyl ether solution (9.2 mL, 18 mmol) was added under ice-cooling, and the mixture was stirred for 30 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.98 g, yield 81%).

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