Hydrochloric Acid → 2-Ethoxycarbonyl-3-methylene-7-oxa-5-norbornene

HRID 1595979Notes

Reaction equation

HRID 1595979 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[CH:2]=[C:3]=[CH2:4].[O:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.Cl>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH2:7]([O:6][C:1]([CH:2]1[C:3](=[CH2:4])[CH:10]2[O:9][CH:13]1[CH:12]=[CH:11]2)=[O:5])[CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8029FuranHCID 4066088Ethyl 2,3-butadienoate

Product 1

HCID 148138112-Ethoxycarbonyl-3-methylene-7-oxa-5-norborneneYield 87.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2,3-butadienoate (0.84 g, 7.5 mmol) and 2.52 g of furan (37 mmol) were combined in a flask under nitrogen and cooled to 0° C. Anhydrous zinc chloride (0.25 g, 1.8 mmol) was added, then the reaction mixture was warmed to room temperature and stirred overnight. NMR analysis indicated that the reaction was complete. Toluene and dilute HCl were added. A black lump of material separated. The toluene and water phases were decanted. The toluene phase was washed with water, filtered and rotovapped. Methylene chloride and aqueous HCl were added to the black solids which dissolved. The methylene chloride phase was washed with water, combined with the rotovapped toluene phase and stripped. A total of 1.18 g of a light brown liquid was obtained.

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. customA black lump of material separated
  3. customThe toluene and water phases were decanted
  4. washThe toluene phase was washed with water
  5. filtrationfiltered
  6. additionMethylene chloride and aqueous HCl were added to the black solids which
  7. dissolutiondissolved
  8. washThe methylene chloride phase was washed with water

Sources & evidence

ORD record
ord-29ca37d3c5664d1885c95940c28190a4
Source dataset
uspto-grants-2001_09
Patent number
US06288260B1

Reaction notes

Loading…