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Triethyl phosphonoacetate → Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)acrylate

HRID 1750072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750072
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[N:35]=[C:34]([NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[C:33]([CH:43]=O)=[CH:32][CH:31]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[N:35]=[C:34]([NH:36][C:37](=[O:42])[C:38]([CH3:39])([CH3:40])[CH3:41])[C:33]([CH:43]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:32][CH:31]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 21073962N-(6-(4-(benzyloxy)butoxy)-3-formylpyridin-2-yl)pivalamide

Produkt 1

HCID 66632284Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)acrylateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

Under N2, an ice-cooled flask containing THF (100 mL) was charged with sodium hydride (5.7 g, 142.5 mmol) to which ethyl 2-(diethoxyphosphoryl)acetate (32 g, 142 mmol) was added. The ice bath was removed and a solution of intermediate 7 (21.8 g, 56.7 mmol) in THF (120 mL) was slowly added to the preformed anion. The reaction was heated to reflux overnight. The reaction mixture was cooled to rt and partitioned between EtOAc and water. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)acrylate (intermediate 8) (13.3 g, 52%) as a white solid. mp: 75-76° C.

Aufarbeitung

  1. additionwas added
  2. customThe ice bath was removed
  3. temperatureThe reaction was heated
  4. temperatureto reflux overnight
  5. custompartitioned between EtOAc and water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4780da745a764f23bf71e65d59b7f4bc
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156822B2

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