Acetic Acid → HCID 86742693, compound

HRID 2292162Notes

Reaction equation

HRID 2292162 reaction equation
N1CCCCC1.C(O)(=O)C.[CH3:11][C:12]([O:15][C:16](=[O:27])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]=O)([CH3:14])[CH3:13].[C:28]([O:34][CH3:35])(=[O:33])[CH2:29][C:30]([CH3:32])=[O:31]>C(O)(C)C>[CH3:11][C:12]([CH3:14])([O:15][C:16](=[O:27])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]=[C:29]([C:30](=[O:31])[CH3:32])[C:28]([O:34][CH3:35])=[O:33])[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 53667508HCID 53667508, compound

Product 1

HCID 86742693HCID 86742693, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of piperidine (0.11 g) and acetic acid (0.078 g) in isopropanol (1 ml) was added to a solution of 3-(2-formylphenyl)propenoic acid 1,1-dimethylethyl ester (5.2 g) and methyl acetoacetate (2.55 g) in isopropanol (15 ml). The mixture was stirred at 60° C. for 1h, then the solvent was evaporated and the residue taken up with ether (100 ml). The solution was washed with 1N HCl, water, with saturated bicarbonate solution, then water again and dried over Na2SO4. Evaporation of the solvent gave an oil which was purified by column chromatography (gradient Petrol/Ether, 7:3-1:1) to give the title compound as a pale oil (4.2 g; mixture E/Z isomers).

Workup

  1. customthe solvent was evaporated
  2. washThe solution was washed with 1N HCl, water, with saturated bicarbonate solution
  3. dry with materialwater again and dried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave an oil which
  6. customwas purified by column chromatography (gradient Petrol/Ether, 7:3-1:1)

Sources & evidence

ORD record
ord-c2292ebf76074e2bbc8f5170144c3c76
Source dataset
uspto-grants-1989_01
Patent number
US04801599

Reaction notes

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