Ethyl Acetate → (1-Methyl-1H-indazol-5-yl)methanol

HRID 1498900Notes

Reaction equation

HRID 1498900 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](OCC)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1.C(OCC)(=O)C>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 68642052HCID 68642052, compound

Product 1

HCID 44119264(1-Methyl-1H-indazol-5-yl)methanolYield 66.1%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (300 mg, 7.83 mmol) was suspended in tetrahydrofuran (20 ml); and under an ice cooling, a solution (10 ml) of ethyl 1-methyl-1H-indazole-5-carboxylate (800 mg, 3.92 mmol) prepared in the Step 4-1-3-A in tetrahydrofuran was slowly added thereto. After the mixture was stirred under an ice cooling for 30 minutes, 5 drops of a saturated sodium bicarbonate solution were slowly added to the mixture. Ethyl acetate was added to the mixture, and 5 drops of a saturated sodium bicarbonate solution was further added thereto. The precipitate was removed by filtration, and the filtrate was concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (420 mg, 66%) as a light-brown powder.

Workup

  1. additionwas slowly added
  2. additionwas further added
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7915fe22a53a4de9a72f63468c919adc
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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