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

HRID 2389879Notes

Reaction equation

HRID 2389879 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 53308849(2-Phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-049714b8f9b244839f8bd81b38518c07
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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