Ethyl diethoxyacetate → HCID 66958526, compound

HRID 1984328Notes

Reaction equation

HRID 1984328 reaction equation
CC(C)([O-])C.[Na+].[CH3:7][C:8]([NH:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:13])[CH2:9][C:10](=[O:12])[CH3:11].[CH2:23]([O:25][CH:26]([O:32][CH2:33][CH3:34])[C:27](OCC)=[O:28])[CH3:24]>C(O)C>[CH2:23]([O:25][CH:26]([O:32][CH2:33][CH3:34])[C:27](=[O:28])[CH2:11][C:10](=[O:12])[CH2:9][C:8]([NH:14][C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:7])[CH3:13])[CH3:24]

Participants

5

Reactant 3

HCID 80169Ethyl diethoxyacetateHCID 12716384N-(2-Methyl-4-oxopentan-2-yl)benzamideHCID 23676156Sodium t-butoxide

Product 1

HCID 66958526HCID 66958526, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium tert-butoxide (5.98 g, 62.2 mmol) was added to a solution of 4-methyl-4-benzamido-2-pentanone (12.4 g, 56.5 mmol) and ethyl diethoxyacetate (11.0 g, 62.2 mmol) in ethanol (40 mL), and the reaction was heated at reflux under a nitrogen atmosphere for 3.5 hours. The solvent was removed under reduced pressure, and the residue was partitioned between saturated aqueous ammonium chloride and tert-butyl methyl ether. The aqueous solution was extracted twice with tert-butyl methyl ether, and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 17.5 g of N-(6,6-diethoxy-1,1-dimethyl-3,5-dioxohexyl)benzamide as a brown oil.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere for 3.5 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between saturated aqueous ammonium chloride and tert-butyl methyl ether
  5. extractionThe aqueous solution was extracted twice with tert-butyl methyl ether
  6. dry with materialthe combined organic fractions were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac2c81be68c24c59a55544690e496046
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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