Hydrochloric Acid → Ethyl 3-trifluoromethyl-2-pentenoate

HRID 888554Notes

Reaction equation

HRID 888554 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.Cl.[F:18][C:19]([F:25])([F:24])[C:20](=O)[CH2:21][CH3:22]>O1CCCC1>[F:18][C:19]([F:25])([F:24])[C:20]([CH2:21][CH3:22])=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 2382881,1,1-Trifluorobutan-2-one2×

Product 1

HCID 76705621Ethyl 3-trifluoromethyl-2-pentenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5.6 g of sodium hydride (60% in oil) in 500 ml of tetrahydrofuran was added dropwise 31.6 g of ethyl diethylphosphonoacetate under ice-cooling. After the mixture was stirred at the same temperature for 10 minutes, the a solution of 1,1,1-trifluoro-2-butanone in diethyl ether obtained in Step 1 was added dropwise thereto. The mixture was stirred at the same temperature for 1 hour, and then warmed to nearly room temperature. To the reaction mixture was added 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain crude ethyl 3-trifluoromethyl-2-pentenoate.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f8e4eb73c8048eab19f56d26623f6c3
Source dataset
uspto-grants-2012_08
Patent number
US08247612B2

Reaction notes

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