Ethyl 2-methylacetoacetate → HCID 21491884, compound

HRID 1973505Notes

Reaction equation

HRID 1973505 reaction equation
C[CH:2]([C:8]([CH3:10])=[O:9])[C:3](OCC)=[O:4].[C:11]1([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1.[O-][CH2:25]C.[Na+]>>[CH:11]1([CH:17]2[C:18]([CH3:25])([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:3](=[O:4])[CH2:2][C:8](=[O:9])[CH2:10]2)[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]1

Participants

4

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 316639AC1L7UAWHCID 2723922Sodium ethoxide

Product 1

HCID 21491884HCID 21491884, compound

Procedure

To a cooled solution of sodium ethoxide (from 2.3 g. sodium and absolute ethanol, 30 ml.) was added with shaking ethyl 2-methylacetoacetate (14.2 g.). When homogeneous the mixture was treated with ethyl 3-(cyclohexenyl)acrylate (16.8 g.) and then heated under reflux for 18 hrs. After cooling the mixture was diluted with 500 ml. water and extracted with ether and the extracts discarded. The aqueous solution was then acidified with 2N-hydrochloric acid and extracted with ether. After washing the ether solution with water and drying over Na2SO4, evaporation of the solution afforded ethyl 6-(3-cyclohexenyl)-2,4-dioxo-1-methylcyclohexanecarboxylate.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hrs
  3. temperatureAfter cooling the mixture
  4. additionwas diluted with 500 ml
  5. extractionwater and extracted with ether
  6. extractionextracted with ether
  7. washAfter washing the ether solution with water
  8. dry with materialdrying over Na2SO4, evaporation of the solution

Sources & evidence

ORD record
ord-ef018c181a41426681eb61f1abb8a316
Source dataset
uspto-grants-1976_12
Patent number
US03997590

Reaction notes

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