Ethyl bromoacetate → HCID 69940430, compound

HRID 840616Notes

Reaction equation

HRID 840616 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.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[O:26]1CCOCC1>>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][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 7748Ethyl bromoacetateHCID 312751,4-DioxaneHCID 226201201-(4-Benzyl-cyclohex-1-enyl)-pyrrolidine

Product 1

HCID 69940430HCID 69940430, compound

Procedure

A solution of 8 g of the crude 1-(4-benzyl-cyclohex-1-enyl)-pyrrolidine and 7 g of ethyl bromoacetate in 20 mL of dioxane was heated at reflux for 12 h, cooled and concentrated under reduced pressure. The 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. Evaporative distillation at oven temperature 150-170° C. at 1 mm gave 8 g of (5-benzyl-2-oxo-cyclohexyl)-acetic acid ethyl ester as a thick oil.

Workup

  1. temperatureat reflux for 12 h
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionThe 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. distillationEvaporative distillation at oven temperature 150-170° C. at 1 mm

Sources & evidence

ORD record
ord-74eae3c2a23e41668260e8e59dcae26f
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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