Methyl 4-(1H-imidazol-1-yl)benzoate → (4-(1H-Imidazol-1-yl)phenyl)methanol

HRID 1781387Notes

Reaction equation

HRID 1781387 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2766374Methyl 4-(1H-imidazol-1-yl)benzoateHCID 68718528lithium aluminium hydride THF

Product 1

HCID 2776486(4-(1H-Imidazol-1-yl)phenyl)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15° C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (0.5 ml), and then diluted with methanol (50 ml) and filtered. Concentration of the filtrate yielded 1.2 g (98%) of 1-(hydroxymethyl)-4-(1H-imidazol-1-yl)-benzene.

Workup

  1. customprepared
  2. customThe reaction was quenched by addition of water (0.5 ml)
  3. additiondiluted with methanol (50 ml)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3e41f9accd6644a589cc4ef9c8e97232
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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