Sodium sulfate decahydrate → (2-Phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol

HRID 2389879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2389879
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[C:24]([C:25](OC)=[O:26])=[C:16]3[C:17]4[CH2:23][CH2:22][O:21][C:18]=4[CH:19]=[CH:20][N:15]3[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:7]1([C:13]2[C:24]([CH2:25][OH:26])=[C:16]3[C:17]4[CH2:23][CH2:22][O:21][C:18]=4[CH:19]=[CH:20][N:15]3[N:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 53310988Methyl 2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

Produkt 1

HCID 53308849(2-Phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanolAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 80% lithium aluminum hydride (100 mg, 2.16 mmol) in tetrahydrofuran (5 mL) was added a solution of methyl 2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate (160 mg, 0.544 mmol) in tetrahydrofuran (5 mL) at room temperature, and the mixture was stirred for 30 min. Sodium sulfate decahydrate (1.7 g) was added under ice-cooling, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, purified by silica gel column chromatography (ethyl acetate), and further washed with diisopropyl ether to give the title compound (132 mg, yield 90%).

Aufarbeitung

  1. temperaturecooling
  2. filtrationthe insoluble material was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (ethyl acetate)
  5. washfurther washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-049714b8f9b244839f8bd81b38518c07
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273761B2

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