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Acetic Acid → (E)-2-Ethyl-3-[4-(3-pyridylmethyl)phenyl]acrylic acid ethyl ester

HRID 2058512
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2058512
[H-].[Na+].[CH2:3]([O:5][C:6]([CH:8](P(=O)(OCC)OCC)[CH2:9][CH3:10])=[O:7])[CH3:4].COC(=O)/C=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][CH:25]=1.C(O)(=O)C>O1CCCC1>[CH2:3]([O:5][C:6](=[O:7])/[C:8](/[CH2:9][CH3:10])=[CH:23]/[C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:28][CH:29]=1)[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

Produkt 1

HCID 12904571(E)-2-Ethyl-3-[4-(3-pyridylmethyl)phenyl]acrylic acid ethyl esterAusbeute 113,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 46 mg of sodium hydride(content 63%) in 3 ml of tetrahydrofuran was added dropwise 0.33 g of diethyl 1-ethoxycarbonylpropylphosphonate at room temperature, and the mixture was stirred at that temperature for 15 minutes. To it was added a solution of 206 mg of the aldehyde (prepared as described in Reference Example 1) in one ml, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was acidified with acetic acid, and concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 273 mg of the title compound having the following physical characteristics:

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-7ea83a51256d4afca9cabe4227eb3716
Quelldatensatz
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04317828

Notizen zur Reaktion

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