tert-Butyl hydroperoxide → 2,3-Epoxy-5-(perfluorooctyl)bicyclo[2.2.1]heptane

HRID 1729112

반응식

HRID 1729112 반응식
[F:1][C:2]([F:27])([C:5]([F:26])([F:25])[C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:3]=[CH2:4].[CH:28]1[CH2:32][CH:31]=[CH:30][CH:29]=1.C([O:37]O)(C)(C)C>C1(C)C=CC=CC=1.CCCCCC>[O:37]1[CH:28]2[CH:29]1[CH:30]1[CH2:31][CH:32]2[CH:3]([C:2]([F:27])([F:1])[C:5]([F:25])([F:26])[C:6]([F:23])([F:24])[C:7]([F:21])([F:22])[C:8]([F:19])([F:20])[C:9]([F:17])([F:18])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH2:4]1

참가 물질

6

반응물 3

HCID 6410tert-Butyl hydroperoxideHCID 7612CyclopentadieneHCID 889901H,1H,2H-Perfluoro-1-decene

생성물 1

HCID 190136952,3-Epoxy-5-(perfluorooctyl)bicyclo[2.2.1]heptane

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8058Hexane용매

실험 절차

128 g (250 mmol) of the Diels-Alder reaction product of 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decene (perfluorooctylethene) and cyclopentadiene are mixed in 10 ml of dry toluene with 815 mg (2.5 mmol) of molybdenum acetylacetonate, and 104 ml of a 3.6 molar solution of t-butyl hydroperoxide in toluene (375 mmol) is added dropwise at 28° C. within 2 hours. During this period, the temperature rises to 40° C. The solution is then held at 65°C. for 14 hours, and subsequently at 80° C. for another 2 hours. Thereaction mixture is filtered over magnesium silicate, followed by washing with two 20 ml portions of toluene. The low-boiling components are stripped off on a rotary evaporator. The residue obtained is taken up in 50 ml of hexane and left to crystallize for 12 hours at -28° C. Theresulting slurry of solids is filtered off with suction and dried at room temperature in an oil pump vacuum.

후처리

  1. additionis added dropwise at 28° C. within 2 hours
  2. waitDuring this period
  3. customrises to 40° C
  4. waitsubsequently at 80° C. for another 2 hours
  5. filtrationThereaction mixture is filtered over magnesium silicate
  6. washby washing with two 20 ml portions of toluene
  7. customThe low-boiling components are stripped off on a rotary evaporator
  8. customThe residue obtained
  9. waitleft
  10. customto crystallize for 12 hours at -28° C
  11. filtrationTheresulting slurry of solids is filtered off with suction
  12. customdried at room temperature in an oil pump vacuum

출처 및 근거

ORD 기록
ord-2610e4cffb77408288eba02348538843
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05331084

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