Ethyl 3-oxovalerate → HCID 13749106, compound

HRID 1732175Notes

Reaction equation

HRID 1732175 reaction equation
C[O-].[Na+].Cl.[Cl:5][C:6]1[C:16]([Cl:17])=[C:15]([C:18](=O)[CH2:19][CH2:20]N(C)C)[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11].O=[C:26]([CH2:33]C)[CH2:27][C:28](OCC)=[O:29]>C(O)C>[Cl:5][C:6]1[C:16]([Cl:17])=[C:15]([C:18]2[CH2:33][CH2:26][CH2:27][C:28](=[O:29])[C:19]=2[CH3:20])[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 78656Ethyl 3-oxovalerateHCID 10942334Sodium MethoxideHCID 70419362HCID 70419362, compound

Product 1

HCID 13749106HCID 13749106, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of sodium methoxide (7.2 g, 0.133 mole) in ethanol (240 ml) and ethyl 3-oxopentanoate (13.5 ml) was added [2,3-dichloro-4-(3-dimethylamino-1-oxopropyl)phenoxy]acetic acid hydrochloride (15.0 g, 0.042 mole). The reaction mixture was heated at reflux for 3 hours, the solvent was distilled at reduced pressure, then the mixture was treated with 150 ml of 2.5% sodium hydroxide and heated on a steam bath for 21/2 hours. The mixture was diluted with water, acidified, extracted into ether, washed with water, brine, dried over magnesium sulfate and evaporated at reduced pressure to give 4.1 g of [2,3-dichloro-4-(2-methyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 143°-145° C. after recrystallization from butyl chloride.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. distillationthe solvent was distilled at reduced pressure
  4. additionthe mixture was treated with 150 ml of 2.5% sodium hydroxide
  5. temperatureheated on a steam bath for 21/2 hours
  6. additionThe mixture was diluted with water
  7. extractionextracted into ether
  8. washwashed with water, brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-a9d12b76a8434b7a922e4b4717908012
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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