Reaktion #4681

ord-9f0b0ca41b4b431daa1c7c12af0a959b

Reaktionsgleichung

CC1CC(OC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)CC(C)(C)C1
3,3,5-trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate
CCOC(=O)/C=C(/C)N
ethyl 3-aminocrotonate
CCO
ethanol
→
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC2CC(C)CC(C)(C)C2)C1c1cccc([N+](=O)[O-])c1
3,3,5-trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
Ausbeute 37.0%

Edukte

CC1CC(OC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)CC(C)(C)C1
3,3,5-trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate
CCOC(=O)/C=C(/C)N
ethyl 3-aminocrotonate
CCO
ethanol

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
-5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

21.87 g (0.06 moles) of 3,3,5-trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate and 7.84 g (0.06 moles) of ethyl 3-aminocrotonate are heated under reflux in 60 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 3,3,5-trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in ethanol--at 125°-129° C. The yield is 37% of the theoretical yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04727066uspto-grants-1988_02