Hydrochloric Acid → HCID 86585361, compound

HRID 635113Notes

Reaction equation

HRID 635113 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 zinc powder (10.59 g) and a catalytic amount of iodine were added thereto. While heating under reflux, a solution (100 ml) of ethyl bromoacetate (13.48 ml, 121 mmol) in tetrahydrofuran was added dropwise thereinto. Then, the liquid reaction mixture was heated under reflux for an additional 1 hour and allowed to cool. After adding 1 N hydrochloric acid (100 ml), the solvent was evaporated and ethyl acetate (500 ml) was added. The insoluble matter was filtered off, washed with a saturated aqueous solution of sodium chloride (300 ml) and dried over anhydrous sodium sulfate. After evaporating the solvent, the title compound was obtained in a quantitative amount as an oily substance.

Workup

  1. temperatureWhile heating
  2. temperatureunder reflux
  3. customThen, the liquid reaction mixture
  4. temperaturewas heated
  5. temperatureunder reflux for an additional 1 hour
  6. temperatureto cool
  7. customthe solvent was evaporated
  8. additionethyl acetate (500 ml) was added
  9. filtrationThe insoluble matter was filtered off
  10. washwashed with a saturated aqueous solution of sodium chloride (300 ml)
  11. dry with materialdried over anhydrous sodium sulfate
  12. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-ef22d18316434a52bed7a0c7618107a4
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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