Water → (3E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

HRID 1828402Notes

Reaction equation

HRID 1828402 reaction equation
C1CN2C(=NCCC2)C1.[C:10](O)([C:12]([F:15])([F:14])[F:13])=[O:11].O.[CH:18]([O:20][CH2:21][CH3:22])=[CH2:19]>C1CCCCC1.CCCCC.CCCCCC.ClCCl>[CH3:22][CH2:21][O:20]/[CH:18]=[CH:19]/[C:10]([C:12]([F:15])([F:14])[F:13])=[O:11]

Participants

9

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 8023Ethyl vinyl ether2×HCID 763491,5-Diazabicyclo(4.3.0)non-5-ene2×

Product 1

HCID 5709222(3E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8003PentaneSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

To begin with, DBN×TFA was prepared in a 250 ml 3-neck flask with a water-cooled condenser. For this purpose, dichloromethane and DBN were added to the flask, and TFA was added dropwise with stirring. Since the reaction is strongly exothermic, the flask was cooled in a water bath to prevent excessive heating. Subsequently, ethyl vinyl ether was added, and TFAH was added dropwise with stirring. The formulation turned yellow. Subsequently, stirring was continued for 1½ hours at room temperature, after which time a sample was taken for gas chromatographic (GC) analysis (sample was hydrolyzed). The ethyl vinyl ether had reacted completely. The dichloromethane was evaporated under vacuum at room temperature in a rotary evaporator, and the remaining solution was divided into partial volumes and extracted with different solvents, which formed two phases. Hexane, pentane, cyclohexane and 113 were used as two-phase extraction agents. The total yield of ETFBO isolated was 91%.

Workup

  1. temperaturecooled condenser
  2. additionwas added dropwise
  3. temperaturethe flask was cooled in a water bath
  4. additionTFAH was added dropwise
  5. stirringwith stirring
  6. stirringSubsequently, stirring
  7. waitwas continued for 1½ hours at room temperature
  8. customThe dichloromethane was evaporated under vacuum at room temperature in a rotary evaporator
  9. extractionextracted with different solvents, which
  10. customformed two phases
  11. extractionextraction agents

Sources & evidence

ORD record
ord-6379dfe218164f05a5d0c2d6aa938b9b
Source dataset
uspto-grants-2006_06
Patent number
US07057079B2

Reaction notes

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