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

HRID 1595979노트

반응식

HRID 1595979 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 1140Toluene용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29ca37d3c5664d1885c95940c28190a4
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288260B1

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