Hydrochloric Acid → HCID 86585361, compound

HRID 1954615Notes

Reaction equation

HRID 1954615 reaction equation
[C:1]([C:4]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])CCC1)(=[O:3])[CH3:2].II.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl.O1C[CH2:26][CH2:25][CH2:24]1>[Zn]>[CH2:20]([O:19][C:17]([C:16]1([CH:4]([CH:1]([OH:3])[CH3:2])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:26][CH2:25][CH2:24]1)=[O:18])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 8028Tetrahydrofuran2×HCID 12116588Ethyl 1-acetylcyclobutanecarboxylate

Product 1

HCID 86585361HCID 86585361, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Ethyl 1-acetylcyclobutanecarboxylate (13.79 g, 81 mmol) was dissolved in tetrahydrofuran (50 ml), and the solution was mixed with zinc powder (10.59 g) and a catalytic amount of iodine. While heating under reflux, a tetrahydrofuran solution (100 ml) of ethyl bromoacetate (13.48 ml, 121 mmol) was added dropwise thereto. The reaction solution was heated under reflux for an additional 1 hour, cooled and then mixed with 1 N hydrochloric acid (100 ml). After evaporating the solvent, the resulting residue was mixed with ethyl acetate (500 ml), washed, after removing insoluble material by filtration, with saturated brine (300 ml) and then dried over anhydrous sodium sulfate. By evaporating the solvent, the title compound was obtained quantitatively in an oily form.

Workup

  1. temperatureWhile heating
  2. temperatureunder reflux
  3. temperatureThe reaction solution was heated
  4. temperatureunder reflux for an additional 1 hour
  5. temperaturecooled
  6. customAfter evaporating the solvent
  7. additionthe resulting residue was mixed with ethyl acetate (500 ml)
  8. washwashed
  9. customafter removing insoluble material
  10. filtrationby filtration
  11. dry with materialwith saturated brine (300 ml) and then dried over anhydrous sodium sulfate
  12. customBy evaporating the solvent

Sources & evidence

ORD record
ord-6aebfbf81ed94e1aa374729d3193c4a4
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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