(Trifluoromethyl)trimethylsilane → HCID 84734005, compound

HRID 1186401Notes

Reaction equation

HRID 1186401 reaction equation
C(O[CH:4]([O:13]CC)[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)C.[F:16][C:17]([Si](C)(C)C)([F:19])[F:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:16][C:17]([F:19])([F:18])[CH:4]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[OH:13]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 84734005HCID 84734005, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 4-(diethoxymethyl)benzaldehyde (400 mg, 1.92 mmol), (trifluoromethyl)trimethylsilane (0.34 mL, 2.3 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 0.19 mL, 0.19 mmol) and tetrahydrofuran (8 mL), the mixture was stirred and reacted at room temperature for 30 minutes. Then, purification by silica gel column chromatography (chloroform/methanol=1/0 to 3/1) was performed to give 4-(2,2,2-trifluoro-1-hydroxyethyl)benzaldehyde (300 mg, yield: 77%).

Workup

  1. customreacted at room temperature for 30 minutes
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=1/0 to 3/1)

Sources & evidence

ORD record
ord-b5dc20debbda4602b290eed23d8f77c7
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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