Water → Ethyl 5-chloro-2-[1-(2-trifluoromethylphenyl)methylidene]pentanoate

HRID 406331Notes

Reaction equation

HRID 406331 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[Cl:13][CH2:14][CH2:15][CH2:16][CH:17](P(OCC)(OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Li+].O>O1CCCC1.C(O)C>[Cl:13][CH2:14][CH2:15][CH2:16][C:17](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[C:2]([F:12])([F:11])[F:1])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 86602479Ethyl 5-chloro-2-(diethoxyphosphoryl)pentanoate

Product 1

HCID 66618943Ethyl 5-chloro-2-[1-(2-trifluoromethylphenyl)methylidene]pentanoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(Trifluoromethyl)benzaldehyde (1 g) and ethyl 5-chloro-2-(diethoxyphosphoryl)pentanoate (CAS No. 870843-20-2, 2.1 g) were dissolved in a mixed solvent of tetrahydrofuran (30 mL) and ethanol (10 mL). Lithium hydroxide (412 mg) was added and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain a geometric isomer mixture of the title compound (1.4 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe drying agent was separated by filtration
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain

Sources & evidence

ORD record
ord-c26771b3fe8042b09ab5aeafb97efad5
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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