Potassium Carbonate → α-(Trifluoromethyl)-3-thiophenemethanol

HRID 1186363Notes

Reaction equation

HRID 1186363 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]([Si](C)(C)C)([F:17])[F:16]>O1CCCC1.CN(C)C=O>[F:14][C:15]([F:17])([F:16])[CH:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[OH:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 681353-ThiophenecarboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 61644908α-(Trifluoromethyl)-3-thiophenemethanolYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Reference Example 8-2, by use of thiophene-3-carbaldehyde (300 mg, 2.67 mmol) dissolved in tetrahydrofuran (4.5 mL) and N,N-dimethylformamide (1.5 mL), potassium carbonate (74 mg, 0.53 mmol) and (trifluoromethyl)trimethylsilane (0.772 mL, 5.34 mmol), the mixture was stirred and reacted at room temperature for 16 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=100/1) was performed to give 2,2,2-trifluoro-1-(thiophen-3-yl)ethanol (Compound DO) (258 mg, yield: 53%).

Workup

  1. customreacted at room temperature for 16 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-5eb2457657f74506a6b605d5c82bd4dc
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…