Hydrochloric Acid → Ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]acrylate

HRID 1826091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1826091
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][C:18](C)([O-])C.[K+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31]C(C=O)=[CH:27][C:26]=1[O:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=1.Cl>O1CCCC1>[CH2:17]([C:3](=[CH:2][C:1]1[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[C:26]([O:33][CH2:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:40][CH:41]=2)[CH:27]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:18]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 118094914-Methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]benzaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 58634019Ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]acrylateAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Under an argon atmosphere, stirring and cooling with ice, a solution of triethyl 2-phosphonobutyrate (555 mg, 2.20 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise to a solution of potassium tert-butoxide (250 mg, 2.23 mmol) in anhydrous tetrahydrofuran (10 mL), and then the mixture was stirred for 20 minutes. Following this, a solution of 4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]benzaldehyde (650 mg, 2.00 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise and then the mixture was stirred for 1 hour under cooling with ice and for 4 hours at room temperature. Cooled 0.5 mol/L hydrochloric acid (30 mL) was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=6:1 v/v) to afford 842 mg (99%) of the title compound as a colorless oily product.

Aufarbeitung

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred for 20 minutes
  3. additionwas added dropwise
  4. stirringthe mixture was stirred for 1 hour
  5. additionwas added to the reaction mixture, which
  6. extractionwas extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=6:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-1d20cabc9b4046bd89a4a277f33fad00
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049342B2

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