Cyclopropyl methyl ketone → 1,3-Dicyclopropylpropane-1,3-dione

HRID 388818

Reaktionsgleichung

Reaktionsgleichung von HRID 388818
[O-]CC.[Na+].[CH3:5][C:6]([CH:8]1[CH2:10][CH2:9]1)=[O:7].[CH:11]1([C:14](OC)=[O:15])[CH2:13][CH2:12]1>CS(C)=O>[CH:11]1([C:14](=[O:15])[CH2:5][C:6]([CH:8]2[CH2:10][CH2:9]2)=[O:7])[CH2:13][CH2:12]1

Komponenten

5

Edukt 3

HCID 13004Cyclopropyl methyl ketoneHCID 76122Methyl cyclopropanecarboxylateHCID 2723922Sodium ethoxide

Produkt 1

HCID 137807821,3-Dicyclopropylpropane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium ethoxide (8 g, 117.64 mmol) was added to a solution of cyclopropyl methyl ketone (5 g, 59.4 mmol) and methyl cyclopropane carboxylate (12 ml, 118.9 mmol) in DMSO (30 mL). The resulting mixture was heated at 60° C. overnight and then cooled to 0° C. After quenching the reaction with 6N HCl, work-up (H2O/AcOEt) gave the title compound as a brown liquid which was used without any purification. 1H-NMR (δ ppm, CDCl3, 400 MHz): 16.05 (bs, 0.6H), 5.72 (s, 0.6H) 3.78 (s, 0.8H), 2.08-2.0 (m, 0.8H), 1.62-1.53 (m, 1.2H), 1.12-1.05 (m, 4H), 0.97-0.83 (m, 4H). MS (m/z): 153.2 [M+H]+.

Aufarbeitung

  1. temperaturecooled to 0° C
  2. customAfter quenching
  3. customthe reaction with 6N HCl, work-up (H2O/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-9036d16a6be14bd48f671b8508a6406c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377970B2

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