Sodium sulfate decahydrate → (1H-Indazol-7-yl)methanol

HRID 246310Notes

Reaction equation

HRID 246310 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10](OCC)=[O:11])[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][OH:11])[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 45790508Ethyl 1H-indazole-7-carboxylate

Product 1

HCID 44119262(1H-Indazol-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, ethyl 1H-indazole-7-carboxylate (600 mg, 3.15 mmol) was dissolved in THF (16 ml). The light yellow solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 3.8 ml, 3.8 mmol) was added dropwise. The bright yellow reaction mixture was stirred at 0° C. for 1.25 h then sodium sulfate decahydrate was carefully added. When gas evolution had stopped, the ice bath was removed, sodium sulfate was added and the mixture was stirred for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to afford (1H-indazol-7-yl)-methanol as a light yellow solid which was used without further purification.

Workup

  1. customthe ice bath was removed
  2. additionsodium sulfate was added
  3. stirringthe mixture was stirred for 30 min at room temperature
  4. filtrationThe suspension was filtered over Celite
  5. washrinsed with ethyl acetate/methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-46ef2a0ba2bc4954b97c02e7f082d5e2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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