Ethyl Acetate → 2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester

HRID 379939Notes

Reaction equation

HRID 379939 reaction equation
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16]>CCCCCC.COCCOC>[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:16]/[C:15]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 115070152-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

After 903 mg (20.7 mmol) of 55% sodium hydride were washed with hexane, it was suspended in 60 ml of 1,2-dimethoxyethane, and 4.63 g (20.7 mmol) of triethyl phosphonoacetate were added dropwise thereto while the suspension was stirred at 0° C. under nitrogen atmosphere. After 15 minutes, 2.00 g (11.5 mmol) of 4-(trifluoromethyl)benzaldehyde were added to the resulting mixture at the same temperature, followed by stirring of the mixture for 15 minutes. Ethyl acetate was added to the reaction mixture and the resulting mixture was washed with water. After drying, an oily residue obtained by evaporation of the solvent was subjected to column chromatography using silica gel and eluted with 4% ethyl acetate-hexane to obtain the title compound having a melting point of 31 to 32.5° C. in a yield of 98%.

Workup

  1. stirringby stirring of the mixture for 15 minutes
  2. washthe resulting mixture was washed with water
  3. customAfter drying
  4. customan oily residue obtained by evaporation of the solvent
  5. washeluted with 4% ethyl acetate-hexane

Sources & evidence

ORD record
ord-37e8d0d2af1c4284a94f5277a544b194
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Reaction notes

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