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Sodium hydride → Ethyl 5-carboethoxy-2-diethylphosphono-2-methylpent-4-enoate

HRID 2286306
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2286306
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Na].[CH2:11]([O:13][P:14]([CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O:16][CH2:17][CH3:18])=[O:15])[CH3:12].[H-].[Na+]>O1CCOCC1>[C:5]([CH:4]=[CH:3][CH2:2][C:19]([P:14]([O:13][CH2:11][CH3:12])([O:16][CH2:17][CH3:18])=[O:15])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O:7][CH2:8][CH3:9])=[O:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionate2×HCID 5360545SodiumHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Produkt 1

HCID 54104589Ethyl 5-carboethoxy-2-diethylphosphono-2-methylpent-4-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

Ethyl 4-bromocrotonate (19.3 parts) was added dropwise at 25°-30° C. to a solution of the sodium salt of ethyl 2-diethylphosphonopropionate, prepared from 23.8 parts of ethyl 2-diethylphosphonopropionate and 5.3 parts of sodium hydride (50% in oil) in dioxan. The resulting solution was heated at reflux for 18 hr., after which time the sodium bromide was removed by filtration and the solution concentrated in vacuo. The residual oil was distilled to give 12.7 parts of ethyl 5-carboethoxy-2-diethylphosphono-2-methylpent-4-enoate boiling at 158°/0.2 mm. Hydrogenation of 12 parts of this material over 5% palladium on carbon gave 7.2 parts of diethyl 2-diethylphosphono-2-methyladipate boiling at 146°-52° C./0.05 mm; subsequent hydrolysis of 5 parts of this in concentrated hydrochloric acid gave 3.7 parts of 2-methyl-2-phosphonoadipic acid as a glassy solid which had a 31P chemical shift of -24 ppm.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 18 hr
  3. custom, after which time the sodium bromide was removed by filtration
  4. concentrationthe solution concentrated in vacuo
  5. distillationThe residual oil was distilled

Quellen und Nachweise

ORD-Eintrag
ord-29733e0f22f443ae9cea146833f391c9
Quelldatensatz
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04265769

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