(Trifluoromethyl)trimethylsilane → HCID 67402892, compound

HRID 1186344Notes

Reaction equation

HRID 1186344 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[O:10])[CH:6]=[N:7][CH:8]=1.[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[N:7][CH:6]=[C:5]([CH:9]([OH:10])[C:12]([F:14])([F:13])[F:11])[CH:4]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 109755495-Methoxy-3-pyridinecarboxaldehyde

Product 1

HCID 67402892HCID 67402892, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 5-methoxy-3-pyridinecarboxaldehyde (300 mg, 2.19 mmol), (trifluoromethyl)trimethylsilane (388 μL, 2.63 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 220 μL, 0.220 mmol) and tetrahydrofuran (6.0 mL), the mixture was stirred and reacted at room temperature for 30 minutes. Then, purification by silica gel column chromatography (chloroform/methanol=9/1) was performed to give 3-methoxy-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound CV) (456 mg, yield: quantitative).

Workup

  1. customreacted at room temperature for 30 minutes
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-71fdfcce6dc44690a116e8fe86cef4b1
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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