Butanoic acid, 4-chloro-4-oxo-, ethyl ester → Diethyl 2-(6-m-methoxyphenyl-3-oxohexyl)-2-methyl-3-oxoadipate

HRID 1077144

Reaktionsgleichung

[CH3:1][CH:2]([C:8](=[O:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OC(CCC(Cl)=O)=O)C.C(N(CC)[CH2:30][CH2:31][C:32](=[O:44])[CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=1)C.[K]>C1C=CC=CC=1.C(O)C.CCOCC>[CH3:43][O:42][C:38]1[CH:37]=[C:36]([CH2:35][CH2:34][CH2:33][C:32](=[O:44])[CH2:31][CH2:30][C:2]([CH3:1])([C:8](=[O:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:41]=[CH:40][CH:39]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

Stir a mixture of diethyl 2-methyl-3-oxoadipate (2.3 g, b.p. 111°-112°C/0.2 mm), prepared from 2- methylacetoacetic ester and ethoxycarbonylpropionyl chloride by the method of Cardwell, J. Chem. Soc., 1949, 715, and the methiodide of 1-diethylamino-6-m-methoxyphenylhexan-3-one (4.6 g) in benzene (20 cc) in an ice bath and add a solution of potassium (0.4 g) in ethanol (10 cc) dropwise over one hour. After stirring for a further 4 hours add ether (50 cc) and evaporate the washed and dried ether extracts. Heat the residue at 160°C and 0.2 mm pressure to remove unchanged starting materials. The residual gum is diethyl 2-(6-m-methoxyphenyl-3-oxohexyl)-2-methyl-3-oxoadipate (2.7 g); infrared absorption peaks at 5.78, 5.88, 6.25, 12.82, 14.49 μ.

Aufarbeitung

stirringAfter stirring for a further 4 hours
customevaporate the
washwashed
custom0.2 mm pressure to remove unchanged
customabsorption peaks at 5.78, 5.88, 6.25, 12.82, 14.49 μ

Quellen und Nachweise

ORD-Eintrag: ord-771e2eb7e34a413897fedbe93ba39a51
Quelldatensatz: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US03959322

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