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Ammonium Chloride → 3-(2,4,6-Trifluoro-phenyl)-acrylic acid ethyl ester

HRID 474577
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 474577
[CH2:1]([O:3][C:4](=[O:12])[CH2:5]P(OC)(OC)=O)[CH3:2].CC([O-])(C)C.[K+].[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:21]=1[CH:22]=O.[Cl-].[NH4+]>C1COCC1.CN(C=O)C.C1COCC1>[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:21]=1/[CH:22]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 67555Ethyl (dimethoxyphosphinoyl)acetateHCID 5218452,4,6-TrifluorobenzaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 574127793-(2,4,6-Trifluoro-phenyl)-acrylic acid ethyl esterAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To the solution of ethyl[bis(methyloxy)phosphoryl]acetate (1.980 mL, 11.99 mmol) in THF-DMF (60 mL, v/v=5:1) at 0° C. was added t-BuOK (1.458 g, 12.99 mmol) portion wise. The resultant mixture was stirred at room temperature for 30 minutes, then mixed with a solution of 2,4,6-trifluorobenzaldehyde (1.6 g, 9.99 mmol) in THF (10 mL) at 0° C. It was allowed to warm to room temperature and the mixture was stirred for 45 min. It was mixed with aqueous ammonium chloride and then extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by a flash column chromatography to give the title compound as a pale yellow oil (2.0 g, 87% yield). LCMS: rt=3.52 min, [M+H+]=231.1

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by a flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e0957e9540054c5f81479c9091b0c6c2
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637536B2

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