Aluminium lithium hydride → 4-(5-Hydroxymethyl-3-methylpyrazol-1-yl)phenol

HRID 1013038Notes

Reaction equation

HRID 1013038 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:3][CH2:4][C:6]1[N:7]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 589487762-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 589487664-(5-Hydroxymethyl-3-methylpyrazol-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (233 mg, 0.946 mmol) was dissolved in tetrahydrofuran (20 mL). Lithium aluminum hydride (1.42 mL, 1 M in THF, 1.42 mmol) was added, and the reaction was stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4) and concentrated to give the crude product in quantitative yield. LC-MS (C11H12N2O2 calculated 204) m/z 205 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbdd3b71288542b8bca9b79faf373247
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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