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

HRID 1595979ノート

反応式

HRID 1595979 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 148138112-Ethoxycarbonyl-3-methylene-7-oxa-5-norbornene収率 87.3%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-29ca37d3c5664d1885c95940c28190a4
出典データセット
uspto-grants-2001_09
特許番号
US06288260B1

反応ノート

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