Sodium sulfate decahydrate → 2-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-methanol

HRID 2389930Notes

Reaction equation

HRID 2389930 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:21]([C:22](OCC)=[O:23])=[C:12]2[C:13]3[CH:19]=[C:18]([CH3:20])[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:21]([CH2:22][OH:23])=[C:12]2[C:13]3[CH:19]=[C:18]([CH3:20])[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 59179437Ethyl 2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 591794472-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-methanolYield 124.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 80% lithium aluminum hydride (293 mg, 7.91 mmol) in tetrahydrofuran (16 mL) was added a solution of ethyl 2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate (430 mg, 1.26 mmol) in tetrahydrofuran (16 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Sodium sulfate decahydrate (4.3 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 (360 mg, yield 99%).

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-157098d007ad4fa488254263c3ffa623
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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