Ethyl Acetoacetate → HCID 23047731, compound

HRID 2107146Notes

Reaction equation

HRID 2107146 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CC[O-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)=[CH:17][CH:16]=1>C(O)C>[C:3]([CH:2]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxideHCID 10753909HCID 10753909, compound

Product 1

HCID 23047731HCID 23047731, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 6.0 g (46 mmol) of ethyl acetoacetate in 6 ml of absolute ethanol is added drop by drop, with stirring, to a solution of 23 mmol of sodium ethylate in 18 ml of ethanol. Stirring is continued for another 15 minutes to complete the salt formation, and then a solution of 6.0 g (23 mmol) of 5-(4-chlorophenyl)pentyl bromide in 6 ml of absolute ethanol is added. The mixture is then heated for 3 hours with refluxing, and then completely concentrated by evaporation. Water is added to the concentrate and the mixture is neutralized with 2N hydrochloric acid. Then the organic components are extracted with ether, the combined extracts are dried, and are concentrated by evaporation. The concentrate is chromatographed on silica gel with a mixture of n-heptane and butanone. Yield: 5.8 g (81% of theory) of ethyl 2-acetyl-7-(4-chlorophenyl)heptanoate, a colorless oil.

Workup

  1. temperatureThe mixture is then heated for 3 hours
  2. temperaturewith refluxing
  3. concentrationcompletely concentrated by evaporation
  4. additionWater is added to the
  5. concentrationconcentrate
  6. extractionThen the organic components are extracted with ether
  7. customthe combined extracts are dried
  8. concentrationare concentrated by evaporation
  9. customThe concentrate is chromatographed on silica gel with a mixture of n-heptane and butanone

Sources & evidence

ORD record
ord-8c33e973386c4c259a9a9d8849ed8177
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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