(Trifluoromethyl)trimethylsilane → HCID 67402338, compound

HRID 1186411Notes

Reaction equation

HRID 1186411 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]1=[O:10].[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][N:2]1[CH:7]=[C:6]([CH:8]([OH:9])[C:12]([F:14])([F:13])[F:11])[CH:5]=[CH:4][C:3]1=[O:10]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 103517561-Methyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde

Product 1

HCID 67402338HCID 67402338, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 1-methyl-5-formyl-2-(1H)-pyridone (309 mg, 2.25 mmol), (trifluoromethyl)trimethylsilane (666 μL, 45.1 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 225 μL, 0.225 mmol) and tetrahydrofuran (10.0 mL), the mixture was stirred and reacted at room temperature fort hour. Then, purification by column chromatography (ethyl acetate) was performed to give 1-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)-2(1H)-pyridone (Compound ET) (214 mg, yield: 46%).

Workup

  1. customreacted at room temperature fort hour
  2. customThen, purification by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-cddb6990f52c4aee978a7e5fcef40fd1
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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