Sodium sulfate decahydrate → (2-ethyl-2H-indazol-4-yl)methanol

HRID 1639770Notes

Reaction equation

HRID 1639770 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Br[C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([CH2:17][CH3:18])[N:13]=2)[C:9]=1[C:19](OC)=[O:20].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:17]([N:12]1[CH:11]=[C:10]2[C:14]([CH:15]=[CH:16][CH:8]=[C:9]2[CH2:19][OH:20])=[N:13]1)[CH3:18]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 59334535methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylate

Product 1

HCID 59334583(2-ethyl-2H-indazol-4-yl)methanolYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.09 g, 28.7 mmol) in tetrahydrofuran (60 mL) was added a solution of methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylate (2.03 g, 7.17 mmol) in tetrahydrofuran (15 mL) under nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 50 hr. Sodium sulfate decahydrate (10 g) was added under ice-cooling, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (ethyl acetate/hexane=25/75→60/40) to give the title compound (1.14 g, yield 90%).

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (ethyl acetate/hexane=25/75→60/40)

Sources & evidence

ORD record
ord-0687db1e1f3a49df95c4bc3491fcef19
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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