(Trifluoromethyl)trimethylsilane → 1-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethan-1-ol

HRID 1186350Notes

Reaction equation

HRID 1186350 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[F:10][C:11]([Si](C)(C)C)([F:13])[F:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:9])[C:11]([F:13])([F:12])[F:10])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 199715811-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethan-1-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 6-chloro-3-pyridinecarboxaldehyde (1.00 g, 7.06 mmol), (trifluoromethyl)trimethylsilane (1.25 mL, 8.48 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 706 μL, 0.706 mmol) and tetrahydrofuran (20 mL), the mixture was stirred and reacted at room temperature for 1 hour. Then, purification by silica gel column chromatography (chloroform/methanol=9/1) was performed to give 2-chloro-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound DC) (1.48 g, yield: 99%).

Workup

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

Sources & evidence

ORD record
ord-873c6a90308647d892dcd7efb6f42099
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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