Potassium Carbonate → 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol

HRID 1186330Notes

Reaction equation

HRID 1186330 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]([Si](C)(C)C)([F:20])[F:19]>CN(C)C=O>[F:17][C:18]([F:20])([F:19])[CH:7]([C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312444-MethoxybenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 2445602,2,2-trifluoro-1-(4-methoxyphenyl)ethanolYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Reference Example 8-2, by use of 4-methoxybenzaldehyde (500 mg, 3.67 mmol) dissolved in N,N-dimethylformamide (7.5 mL), potassium carbonate (101 mg, 0.734 mmol) and (trifluoromethyl)trimethylsilane (1.09 mL, 7.34 mmol), the mixture was stirred and reacted at room temperature, at 80° C. for 7 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=100/1) was performed to give 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol (Compound CJ) (636 mg, yield: 84%).

Workup

  1. customreacted at room temperature, at 80° C. for 7 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-a9aa80ce18e7429a9f4c197c35d420bb
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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