2-Thiophenecarboxaldehyde → 2-Thiophenemethanol, a-(trifluoromethyl)-

HRID 1186362Notes

Reaction equation

HRID 1186362 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].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:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[OH:7]

Participants

6

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 11430Potassium CarbonateHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 109541472-Thiophenemethanol, a-(trifluoromethyl)-Yield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Reference Example 8-2, by use of thiophene-2-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 extraction gave 2,2,2-trifluoro-1-(thiophen-2-yl)ethanol (Compound DN) (378 mg, yield: 78%).

Workup

  1. customreacted at room temperature for 16 hours
  2. customThen, purification
  3. extractionby extraction

Sources & evidence

ORD record
ord-f824ac6d7e3b4dc39c2a1b04ff792bfc
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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