3-Chloro-2-methyl-1-propene → Diethyl (2-methylprop-2-en-1-yl)(propan-2-yl)propanedioate

HRID 441841

Reaktionsgleichung

Reaktionsgleichung von HRID 441841
[CH:1]([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:3])[CH3:2].CN(P(N(C)C)N(C)C)C.[H-].[Na+].[CH2:27](Cl)[C:28](=[CH2:30])[CH3:29]>C1(C)C=CC=CC=1.CN(P(N(C)C)N(C)C)C.C1(C)C=CC=CC=1>[CH:1]([C:4]([CH2:29][C:28]([CH3:30])=[CH2:27])([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 12966Diethyl isopropylmalonateHCID 15355Hexamethylphosphorous triamideHCID 24758Sodium hydride

Produkt 1

HCID 54297538Diethyl (2-methylprop-2-en-1-yl)(propan-2-yl)propanedioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 131710867HMPT tolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of diethyl isopropylmalonate (8.1g) in 25 ml of a 25% solution of HMPT (hexamethylphosphorus triamide) in toluene was added dropwise over 15 minutes to a suspension of sodium hydride (50 mM) in 25% HMPT/toluene (50 ml) at room temperature. The mixture was then stirred at 60° C. for 1/2 hour, cooled to 25° C. and methallyl chloride (4.0g) in 25% HMPT/toluene was added over 10 minutes. The mixture was stirred at 80°-85° C. overnight, cooled to room temperature and poured onto a mixture of ice/hydrochloric acid. The product was extracted with ether, the ethereal extracts washed with water, followed by 2N sodium hydroxide and then water, and dried over magnesium sulphate. Removal of solvent gave diethyl isopropyl-2-methylprop-2-enylmalonate as a pale yellow liquid. R.I. nD21 1.4467.

Aufarbeitung

  1. temperaturecooled to 25° C.
  2. stirringThe mixture was stirred at 80°-85° C. overnight
  3. temperaturecooled to room temperature
  4. extractionThe product was extracted with ether
  5. washthe ethereal extracts washed with water
  6. dry with materialwater, and dried over magnesium sulphate
  7. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-e4fab342618b4a428769a1d589c27839
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04042710

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