Aluminium lithium hydride → [5-methyl-1-(propan-2-yl)-1H-pyrazol-3-yl]methanol

HRID 706548

Reaction equation

HRID 706548 reaction equation
[CH:1]([N:4]1[C:8]([CH3:9])=[CH:7][C:6]([C:10](OCC)=[O:11])=[N:5]1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([N:4]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][OH:11])=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23005696Ethyl 1-isopropyl-5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 23005569[5-methyl-1-(propan-2-yl)-1H-pyrazol-3-yl]methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 1-isopropyl-5-methyl-1H-pyrazole-3-carboxylate (7.68 g, 39.1 mmol) in THF (50 mL) at 0° C. was added LAH (1.49 g, 39.1 mmol). The cold bath was removed, and the reaction mixture was stirred for 2 hours, and then quenched carefully with sodium sulfate decahydrate. The reaction mixture was filtered through Celite and washed with Et2O. The filtrate was concentrated under reduced pressure to give 5.3 g (88%) of the title compound.

Workup

  1. customThe cold bath was removed
  2. customquenched carefully with sodium sulfate decahydrate
  3. filtrationThe reaction mixture was filtered through Celite
  4. washwashed with Et2O
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eddea3fe6be443afb27ba168522ac205
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Linked notes

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