Hydrochloric Acid → HCID 11010183, compound

HRID 1457981Notes

Reaction equation

HRID 1457981 reaction equation
[C:1]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].II.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C1C=CC=CC=1.BrCC(OCC)=O.Cl>C1C=CC=CC=1.[Zn]>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][C:1]([OH:3])([CH3:2])[C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)[CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateHCID 22100536HCID 22100536, compound

Product 1

HCID 11010183HCID 11010183, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 241BenzeneSolvent2×

Procedure

A 61.7 g (0.39 mol) portion of ethyl 1-acetylcyclopropanecarboxylate was dissolved in 500 ml of benzene to which were subsequently added 13 g of zinc powder and a catalytically effective amount of iodine. While heating under reflux, a solution of 56.2 ml (0.51 mol) of ethyl bromoacetate in 100 ml of benzene was added dropwise to the mixture above. When the reaction started to progress, the dropwise addition was suspended, 39 g of zinc powder was added in small portions and then the remaining ethyl bromoacetate benzene solution was added dropwise. After completion of the addition, the reaction solution was heated under reflux for another 2 hours. The reaction solution was cooled spontaneously, mixed with 500 ml of 1N hydrochloric acid and then filtered through celite. The organic layer was separated, washed with saturated brine (500 ml×2) and then dried over anhydrous sodium sulfate. By evaporating the solvent, 90.31 g (95%) of the title compound was obtained as an oily substance.

Workup

  1. temperatureWhile heating
  2. temperatureunder reflux
  3. additionthe dropwise addition
  4. additionAfter completion of the addition
  5. temperaturethe reaction solution was heated
  6. temperatureunder reflux for another 2 hours
  7. temperatureThe reaction solution was cooled spontaneously
  8. filtrationfiltered through celite
  9. customThe organic layer was separated
  10. washwashed with saturated brine (500 ml×2)
  11. dry with materialdried over anhydrous sodium sulfate
  12. customBy evaporating the solvent

Sources & evidence

ORD record
ord-1f9e89dbb24949d3a41b185a25e798ba
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

Loading…