Acetic Acid → HCID 10922777, compound

HRID 1251025Notes

Reaction equation

HRID 1251025 reaction equation
[C:1]1([C:7]([CH:9]([CH2:13][CH2:14][C:15](=[O:17])[CH3:16])[C:10]([O-:12])=[O:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](O)(=O)[CH3:19].CCOC(C)=O>C1(C)C=CC=CC=1.N1CCCCC1>[O:17]=[C:15]1[CH2:14][CH2:13][CH:9]([C:10]([O:12][CH2:18][CH3:19])=[O:11])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 86583681HCID 86583681, compound

Product 1

HCID 10922777HCID 10922777, compoundYield 758.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-(phenylcarbonyl)-5-oxohexanoate(3.87 g, 14.8 mmol), acetic acid(130 mg, 2.17 mmol) and piperidine(127 mg, 1.49 mmol) in toluene(5 ml) was refluxed for 5 hr. After cooling down to room temperature, AcOEt was added to the reaction mixture and washed with dil. HCI, water and brine and dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 4.02 g of ethyl 4-oxo-2-phenylcyclohex-2-enecarboxylate(y=94.7%) as a brown oil. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.50(2H, dd, J=3.0 and 6.4 Hz), 7.40-7.48(3H), 6.47(1H, s), 4.11(2H, q, J=7.0 Hz), 3.96(1H, dd, J=3.7 and 3.7 Hz), 2.60-2.70(1H, m), 2.35-2.55(3H), 1.12(3H, t, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 5 hr
  2. washwashed with dil. HCI, 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-f448142660e84aeaa6ddfca46439bb52
Source dataset
uspto-grants-2002_01
Patent number
US06340772B1

Reaction notes

Loading…