Acetic Acid → HCID 11821270, compound

HRID 650316Notes

Reaction equation

HRID 650316 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. iH-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-c17fb5e97d274bc49b24cfbed7924226
Source dataset
uspto-grants-2001_08
Patent number
US06271418B1

Reaction notes

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