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

HRID 1768123Notes

Reaction equation

HRID 1768123 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fe2503a67b6d4fc19de7c6163589c3ee
Source dataset
uspto-grants-2007_06
Patent number
US07235570B2

Reaction notes

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