2-Pyridinecarboxaldehyde → 2,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-ol

HRID 1186336Notes

Reaction equation

HRID 1186336 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[F:9][C:10]([Si](C)(C)C)([F:12])[F:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:9][C:10]([F:12])([F:11])[CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[OH:8]

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 137429262,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-olYield 126.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 2-pyridinecarboxaldehyde (500 μL, 5.26 mmol), (trifluoromethyl)trimethylsilane (932 μL, 6.31 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 526 μL, 0.526 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature for 10 minutes. Then, purification by silica gel column chromatography (chloroform/methanol=9/1) was performed to give 2-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound CN) (1.18 g, yield: quantitative).

Workup

  1. customreacted at room temperature for 10 minutes
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-358ac4f581e94a6c855b75484f4aef9e
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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