Acetic Acid → Ethyl isopropyl 1,4-dihydro-4-(2'-ethoxy-6'-pentadecylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

HRID 1768123

Reaktionsgleichung

Reaktionsgleichung von HRID 1768123
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:5]=1[CH:6]=O)[CH3:2].[C:27]([O:33][CH:34]([CH3:36])[CH3:35])(=[O:32])[CH2:28][C:29]([CH3:31])=O.C(O)(=O)C.N1CCCCC1.[CH3:47][CH2:48][O:49][C:50](/[CH:52]=[C:53](\[NH2:55])/[CH3:54])=[O:51]>C(O)CCC>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:5]=1[CH:6]1[C:28]([C:27]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[C:29]([CH3:31])[NH:55][C:53]([CH3:54])=[C:52]1[C:50]([O:49][CH2:48][CH3:47])=[O:51])[CH3:2]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 68329Isopropyl acetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 225745702-Ethoxy-6-pentadecyl benzaldehyde

Produkt 1

HCID 10282132Ethyl isopropyl 1,4-dihydro-4-(2'-ethoxy-6'-pentadecylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

2-Ethoxy-6-pentadecyl benzaldehyde (3 g, 8.3 mmol) and isopropyl acetoacetate (1.19 g, 8.3 mmol) were dissolved in n-butanol (20 mL). Acetic acid (0.5 g, 8.3 mmol) and piperidine (0.7 g, 8.3 mmol) were added and stirred at room temperature for 3-4 hrs. Ethyl-3-amino crotonate (1.08 g, 8.3 mmol) was then added and refluxed for 10 hrs. n-Butanol was evaporated and reaction mixture was washed with distilled water and extracted with dichloromethane (10 mL). Organic layer was dried over sodium sulfate, evaporated and compound was purified by column chromatography using silica gel (100-200 mesh) with hexane:EtOAc (94:6) solvent system to give ethyl isopropyl 1,4-dihydro-4-(2′-ethoxy-6′-pentadecylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate as viscous liquid.

Aufarbeitung

  1. temperaturerefluxed for 10 hrs
  2. customn-Butanol was evaporated
  3. customreaction mixture
  4. washwas washed with distilled water
  5. extractionextracted with dichloromethane (10 mL)
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. customevaporated
  8. customcompound was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fe2503a67b6d4fc19de7c6163589c3ee
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235570B2

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