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

HRID 2389876
Notes
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Reaction equation

HRID 2389876 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[CH:23]=[CH: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[CH:23]=[CH: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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 59179362Methyl 2-phenylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 59179389(2-Phenylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanolYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 80% lithium aluminum hydride (294 mg, 6.35 mmol) in tetrahydrofuran (10 mL) was added a solution of methyl 2-phenylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate (465 mg, 1.59 mmol) in tetrahydrofuran (10 mL) at room temperature, and the mixture was stirred at 50° C. for 5 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 purified by recrystallization (ethyl acetate) to give the title compound (367 mg, yield 87%).

Workup

  1. temperaturecooling
  2. filtrationthe insoluble material was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-494313a2683f4ff6b67b55e9269d5ba9
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273761B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes