Acetic Acid → HCID 9959726, compound

HRID 23780Notes

Reaction equation

HRID 23780 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([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][CH2:26][CH3:27])[C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:28]([O:34][CH3:35])(=[O:33])[CH2:29][C:30]([CH3:32])=O.[C:36]([OH:39])(=[O:38])[CH3:37].[NH:40]1CCC[CH2:42][CH2:41]1.[CH3:46]C=CC(ONC)=O>C(O)CCC>[CH:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([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][CH2:26][CH3:27])[C:6]=1[CH:7]1[C:29]([C:28]([O:34][CH3:35])=[O:33])=[C:30]([CH3:32])[NH:40][C:41]([CH3:42])=[C:37]1[C:36]([O:39][CH3:46])=[O:38])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 22574564HCID 22574564, compoundHCID 53434921HCID 53434921, compound

Product 1

HCID 9959726HCID 9959726, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Isopropoxy-6-pentadecyl benzaldehyde (3.1 g, 8.3 mmol) and methyl acetoacetate (0.96 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. methyl-3-amino crotonate (0.97 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 silicagel (100-200 mesh) with hexane:EtOAc (94:6) solvent system to give dimethyl 1,4-dihydro-4-(2′-isopropoxy-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-8ba0f582bc144ba682e632855fd02a0f
Source dataset
uspto-grants-2005_02
Patent number
US06852742B2

Reaction notes

Loading…