Ethyl bromoacetate → HCID 69940430, compound
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
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.