Water → (2-Methyl-2H-indazol-4-yl)methanol

HRID 1639737Notes

Reaction equation

HRID 1639737 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[C:17](OC)=[O:18])=[N:9]1.O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH3:7][N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[CH2:17][OH:18])=[N:9]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 37818684Methyl 2-methyl-2H-indazole-4-carboxylate

Product 1

HCID 44119267(2-Methyl-2H-indazol-4-yl)methanolYield 90.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (14.27 g, 421 mmol) in tetrahydrofuran (315 mL) was added a solution of methyl 2-methyl-2H-indazole-4-carboxylate (40.0 g, 210 mmol) in tetrahydrofuran (106 mL) under nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with diethyl ether at 0° C., water (15 mL), 10% aqueous sodium hydroxide solution (15 mL) and water (30 mL) were added and the mixture was stirred until gas generation stopped. The resulting precipitate was collected by filtration, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was triturated with ethyl acetate and hexane to give the title compound (30.7 g, yield 90%).

Workup

  1. stirringthe mixture was stirred until gas generation
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-b06d504c855c41d5a06de6feacfcbae5
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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