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

HRID 406331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406331
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c26771b3fe8042b09ab5aeafb97efad5
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754100B2

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