Potassium Carbonate → 1-Methyl-α-(trifluoromethyl)-1H-imidazole-5-methanol

HRID 1186359Notes

Reaction equation

HRID 1186359 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]=[CH:3]1.C(=O)([O-])[O-].[K+].[K+].[F:15][C:16]([Si](C)(C)C)([F:18])[F:17]>CN(C)C=O>[F:15][C:16]([F:18])([F:17])[CH:7]([C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)[OH:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 5735921-methyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 661182051-Methyl-α-(trifluoromethyl)-1H-imidazole-5-methanolYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Reference Example 8-2, by use of 1-methyl-1H-imidazole-5-carbaldehyde (300 mg, 2.72 mmol) dissolved in N,N-dimethylformamide (4.5 mL), potassium carbonate (75 mg, 0.54 mmol) and (trifluoromethyl)trimethylsilane (0.442 mL, 2.99 mmol), the mixture was stirred and reacted at room temperature for 3 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=10/1) was performed to give 2,2,2-trifluoro-1-(1-methyl-1H-imidazol-5-yl)ethanol (Compound DK) (358 mg, yield: 73%).

Workup

  1. customreacted at room temperature for 3 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-df06e3b8e7be4b368e0020750028621f
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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