2-Methylfuran → (1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene

HRID 1470850

반응식

HRID 1470850 반응식
[Cl:1][CH:2]1[C:4]([Cl:6])([Cl:5])[C:3]1([Cl:8])Cl.[OH-:9].[K+].[CH3:11][C:12]1OC=C[CH:16]=1.O1[CH2:22][CH2:21]OCC1>>[Cl:1][C:2]1[C@:21]2([CH3:22])[O:9][C@H:16]([C:4]([Cl:6])([Cl:5])[C:3]=1[Cl:8])[CH:12]=[CH:11]2

참가 물질

5

반응물 4

HCID 107972-MethylfuranHCID 14797Potassium HydroxideHCID 22631PentachlorocyclopropaneHCID 312751,4-Dioxane

생성물 1

HCID 67533581(1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene

실험 절차

Pentachlorocyclopropane (100 g, 0.467 mol) is added to a suspension of potassium hydroxide (31.4 g, 0.56 mol) in 1,4-dioxane (3600 ml) and the mixture is stirred at room temperature for 30 minutes and then heated to 65° C. for a further 30 minutes. 2-Methylfuran (38.36 g, 0.467 mol) is added to the reaction mixture, the temperature is raised to 85-90° C. and the mixture is stirred for 16 hours. The reaction mixture is cooled to room temperature, filtered through a plug of diatomaceous earth and the filtrate evaporated in vacuo to give (1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene (83 g), used without further purification in the next step.

후처리

  1. temperatureheated to 65° C. for a further 30 minutes
  2. temperaturethe temperature is raised to 85-90° C.
  3. stirringthe mixture is stirred for 16 hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. filtrationfiltered through a plug of diatomaceous earth
  6. customthe filtrate evaporated in vacuo

출처 및 근거

ORD 기록
ord-bc3e11c4f9b8412dbfaf95f5e55bbadf
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006429B2

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