Acetic Acid → HCID 11821270, compound

HRID 1251024Notes

Reaction equation

HRID 1251024 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[C:11]([O-:13])=[O:12])=O)=[CH:4][CH:3]=1.[C:19](O)(=O)[CH3:20].N1CCCCC1.CCOC(C)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:10]([C:11]([O:13][CH2:19][CH3:20])=[O:12])[CH2:14][CH2:15][C:16](=[O:18])[CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 86583680HCID 86583680, compound

Product 1

HCID 11821270HCID 11821270, compoundYield 587.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-((4-methylphenyl)carbonyl)-5-oxohexanoate(4.19 g, 15.2 mmol), acetic acid(137 mg, 2.28 mmol) and piperidine(129 mg, 1.52 mmol) in toluene(10 ml) was refluxed for 9 hr. After cooling down to room temperature, AcOEt was added to the reaction mixture and washed with dil. HCl, water and brine, dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 3.46 g of ethyl 2-(4-methylphenyl)-4-oxocyclohex-2-enecarboxylate(y=88.0%) as a brown oil. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.41(2H, d, J=8.2 Hz), 7.21(2H, d, J=8.2 Hz), 5.47(1H, s), 4.11(2H, q, J=7.0 Hz), 3.96(1H, dd, J=4.8 and 4.8 Hz), 2.55-2.65(1H, m), 2.40-2.55(3H, m), 2.38(3H, s), 1.14(3H, t, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 9 hr
  2. washwashed with dil. HCl, water and brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel with n-hexane-AcOEt

Sources & evidence

ORD record
ord-d3fa4d35bd6946f9b3b20128c3bfcf05
Source dataset
uspto-grants-2002_01
Patent number
US06340772B1

Reaction notes

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