Diethyl isopropylmalonate → Diethyl 2-isopropyl-2-propylmalonate

HRID 866696

Reaktionsgleichung

Reaktionsgleichung von HRID 866696
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([CH:11]([CH3:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].CN(P(N(C)C)N(C)C)C.[H-].[Na+].[CH3:27][CH2:28][CH2:29]I>C1(C)C=CC=CC=1.CN(P(N(C)C)N(C)C)C.C1(C)C=CC=CC=1>[CH:11]([C:5]([CH2:27][CH2:28][CH3:29])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:4]([O:3][CH2:1][CH3:2])=[O:14])([CH3:12])[CH3:13]

Komponenten

7

Edukt 4

HCID 12966Diethyl isopropylmalonateHCID 15355Hexamethylphosphorous triamideHCID 24758Sodium hydrideHCID 336431-Iodopropane

Produkt 1

HCID 599161Diethyl 2-isopropyl-2-propylmalonateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 131710867HMPT tolueneLösungsmittel

Versuchsvorschrift

A solution of diethylisopropylmalonate (10.1g) in 15 ml of a 25% solution of HMPT (hexamethylphosphorus triamide) in toluene was added dropwise over 15 minutes to a suspension of sodium hydride (70mM) in 25% HMPT/toluene (15ml) at 50°-70° C. N-propyl iodide (17.0g) was then added over 30 minutes at 70°-100° C and the mixture stirred at 120°-130° C for 11/2 hours. After cooling, methylated spirits (10ml) was added and the mixture poured onto a mixture of ice/hydrochloric acid. The product was extracted with ether, the ethereal extracts washed with sodium bicarbonate (X2), then water and dried over anhydrous magnesium sulphate. Removal of the solvent gave diethyl 2-isopropyl-2-propylmalonate as a yellow liquid b.p. 92°-94°/1 mm Hg. 87% yield.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe product was extracted with ether
  3. washthe ethereal extracts washed with sodium bicarbonate (X2)
  4. dry with materialwater and dried over anhydrous magnesium sulphate
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-21d7cd48be5f4b0fbafaec30ff07e0b7
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04100363

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