(Trifluoromethyl)trimethylsilane → 1-Diethoxymethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)benzene

HRID 1186340Notes

Reaction equation

HRID 1186340 reaction equation
[CH3:1][CH2:2][O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1.[F:16][C:17]([Si](C)(C)C)([F:19])[F:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:14]([O:13][CH:4]([O:3][CH2:2][CH3:1])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:12])[C:17]([F:19])([F:18])[F:16])=[CH:7][CH:6]=1)[CH3:15]

Participants

5

Reactant 3

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

Product 1

HCID 674006431-Diethoxymethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Step 2 of Reference Example 8-17, by use of terephthalaldehyde mono(diethyl acetal) (796 μL, 4.00 mol), (trifluoromethyl)trimethylsilane (709 μL, 4.80 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 4.40 mL, 4.40 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature for 2.5 hours. Then, purification by silica gel column chromatography (hexane/ethyl acetate=4/1) was performed to give 1-diethoxymethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)benzene (Compound CR) (1.04 g, yield: 93%).

Workup

  1. customreacted at room temperature for 2.5 hours
  2. customThen, purification by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e9a3c2a43116444293d757fea74668b8
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…