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

HRID 1601365Notes

Reaction equation

HRID 1601365 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-8e24e4f2443a4224b4ff0bf5e16db9b6
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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