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

HRID 2389878Notes

Reaction equation

HRID 2389878 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:20]([C:21](OCC)=[O:22])=[C:12]2[C:13]3[CH2:19][CH2:18][O:17][C:14]=3[CH:15]=[CH:16][N:11]2[N:10]=1)[CH3:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:7]([C:9]1[C:20]([CH2:21][OH:22])=[C:12]2[C:13]3[CH2:19][CH2:18][O:17][C:14]=3[CH:15]=[CH:16][N:11]2[N:10]=1)[CH3:8]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 53310990Ethyl 2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 53308851(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanolYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 80% lithium aluminum hydride (548 mg, 11.8 mmol) in tetrahydrofuran (30 mL) was added a solution of ethyl 2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate (770 mg, 2.96 mmol) in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Sodium sulfate decahydrate (10 g) was added under ice-cooling, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was washed with diisopropyl ether to give the title compound (485 mg, yield 75%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-5083c956ec1f434783ea5c6f29c274ea
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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