(Trifluoromethyl)trimethylsilane → HCID 67402379, compound

HRID 1186342Notes

Reaction equation

HRID 1186342 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=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:4]=[CH:5][C:6]([CH:9]([OH:10])[C:12]([F:14])([F:13])[F:11])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 67402379HCID 67402379, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 6-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 3 hours. Then, purification by silica gel column chromatography (hexane/ethyl acetate=4/1) was performed to give 2-methoxy-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound CT) (424 mg, yield: 93%).

Workup

  1. customreacted at room temperature for 3 hours
  2. customThen, purification by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d28c5aad90854f24aa7d37050af3b41c
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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