Ethyl Acetate → HCID 68984654, compound

HRID 2249648Notes

Reaction equation

HRID 2249648 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]([O:21][C:22]1[CH:45]=[C:44]([O:46][CH2:47][CH:48]([CH3:50])[CH3:49])[CH:43]=[CH:42][C:23]=1[C:24]([C:26]1[CH:27]=[CH:28][C:29]([O:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[C:30]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH:31]=1)=O)[CH:18]([CH3:20])[CH3:19].C(OCC)(=O)C>CN(C)C=O.O>[CH2:17]([O:21][C:22]1[CH:45]=[C:44]([O:46][CH2:47][CH:48]([CH3:49])[CH3:50])[CH:43]=[CH:42][C:23]=1[C:24]([C:26]1[CH:27]=[CH:28][C:29]([O:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[C:30]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH:31]=1)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:18]([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 57684398HCID 57684398, compound

Product 1

HCID 68984654HCID 68984654, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 5 ml of N,N-dimethylformamide is suspended 0.85 g of 60% sodium hydride, to which is dropwise added 4.2 ml of ethyl diethylphosphonoacetate at ambient temperature over a period of 10 minutes. After stirring the mixture thus obtained for 30 minutes, 1.00 g of 3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoic acid is added and stirred at 110° C. for 5 hours. The reaction mixture is cooled to ambient temperature and added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.36 g of 3-{5-[1-(2,4-diisobutoxyphenyl)-3-ethoxy-3-oxo-1-propenyl]-2-isobutoxyphenyl}propanoic acid as a light yellow oily product.

Workup

  1. customat ambient temperature
  2. customof 10 minutes
  3. customthus obtained for 30 minutes
  4. stirringstirred at 110° C. for 5 hours
  5. customthe organic layer is separated
  6. customThe organic layer thus obtained
  7. washis washed with water and saturated aqueous solution of sodium chloride successively
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8990dedf41184d01aa95560a3f234593
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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