Sodium sulfate decahydrate → 8,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol

HRID 2389877Notes

Reaction equation

HRID 2389877 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:19](OCC)=[O:20])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][CH2:18][C:12]=3[C:11]=12.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:7]1([CH2:19][OH:20])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][CH2:18][C:12]=3[C:11]=12

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 59179449Ethyl 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 591793818,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanolYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 80% lithium aluminum hydride (760 mg, 16.4 mmol) in tetrahydrofuran (40 mL) was added a solution of ethyl 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate (950 mg, 4.09 mmol) in tetrahydrofuran (40 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 (650 mg, yield 83%).

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-329a085c42e34884a8639f9bdc7f7410
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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