Ethyl Acrylate → 3-(5-Benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester

HRID 840620Notes

Reaction equation

HRID 840620 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11](N2CCCC2)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21].[O:26]1CCOCC1>>[CH2:24]([O:23][C:19](=[O:22])[CH2:20][CH2:21][CH:10]1[CH2:9][CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12][C:11]1=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 8821Ethyl AcrylateHCID 312751,4-DioxaneHCID 226201201-(4-Benzyl-cyclohex-1-enyl)-pyrrolidine

Product 1

HCID 699404643-(5-Benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester

Procedure

A solution of 1 g of the crude 1-(4-benzyl-cyclohex-1-enyl)-pyrrolidine and 1 mL of ethyl acrylate in 20 mL of dioxane was heated at reflux for 3 h, cooled and concentrated under reduced pressure. The resulting residue was diluted with 10 mL of water and 10 mL of 10% sulfuric acid and extracted into 2×100 mL of ether. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum gave 0.74 g of crude 3-(5-benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 3 h
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting residue was diluted with 10 mL of water and 10 mL of 10% sulfuric acid
  5. extractionextracted into 2×100 mL of ether
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customDrying under vacuum

Sources & evidence

ORD record
ord-f84694bdae22450280d18a80bffe2e2e
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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