Sodium hydride → Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)butenoate

HRID 745623

Reaktionsgleichung

Reaktionsgleichung von HRID 745623
C(OP([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:18][CH:19]([CH3:33])[CH2:20][C:21](=O)[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C1(C)C=CC=CC=1>[CH2:13]([O:12][C:10]([C:9]([CH3:15])=[C:21]([CH2:20][CH:19]([CH3:33])[CH3:18])[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:11])[CH3:14]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 4072499Benzyl 4-methyl-2-oxopentanoate

Produkt 1

HCID 53831566Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)butenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Ethyl 2-(diethylphosphono)propanoate (23.9 g.) was added to dry toluene (250 mls.) containing 80% sodium hydride in mineral oil (3.0 g.) at room temperature. The resultant mixture was heated to 50°-60° C. for 5 minutes and then cooled to -30° to -40° C. To the cooled mixture was added benzyl 4-methyl-2-oxopentanoate (20 g.) and the resulting mixture was allowed to warm to room temperature over a period of 1 hour. The toluene solution was washed with dilute citric acid (50 mls.), water (2×50 mls.) and then dried over anhydrous sodium sulfate. The toluene was removed by evaporation in vacuo to yield E and Z benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)butenoate as a mixture of isomers in the form of an oil.

Aufarbeitung

  1. temperaturecooled to -30° to -40° C
  2. washThe toluene solution was washed with dilute citric acid (50 mls.), water (2×50 mls.)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe toluene was removed by evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ce6b4ff7663d44a0b47df91821f3ec21
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04599361

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