Dimethyl Sulfide → trans-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-4-(3-oxo-cyclopent-1-enyloxy)-2H-1-benzopyran-3-ol

HRID 363457

반응식

HRID 363457 반응식
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.[H-].[Na+].CSC.[O:13]1[CH:19]2[CH:14]1[C:15]([CH2:33][F:34])([CH2:31][F:32])[O:16][C:17]1[CH:23]=[CH:22][C:21]([C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])=[CH:20][C:18]=12.S(=O)(=O)(O)O>O1CCCC1.[Cu]Br.O>[F:30][C:24]([F:29])([C:21]1[CH:22]=[CH:23][C:17]2[O:16][C:15]([CH2:33][F:34])([CH2:31][F:32])[C@@H:14]([OH:13])[C@H:19]([O:6][C:3]3[CH2:4][CH2:5][C:1](=[O:7])[CH:2]=3)[C:18]=2[CH:20]=1)[C:25]([F:28])([F:27])[F:26]

참가 물질

9

반응물 5

HCID 1068Dimethyl SulfideHCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 774661,3-CyclopentanedioneHCID 158717923,4-epoxy-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-2H-1-benzopyran

생성물 1

HCID 86750614trans-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-4-(3-oxo-cyclopent-1-enyloxy)-2H-1-benzopyran-3-ol수율 3.4%

시약·촉매·용매 3

HCID 24593copper(I) bromide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

In 40 ml of tetrahydrofuran was dissolved 0.36 g of cyclopentan-1,3-dione and 0.13 g of sodium hydride (60%) was added thereto under nitrogen stream with cooling at -20° C. After the mixture was stirred at room temperature for 15 minutes, 0.72 g of a complex of copper (I) bromide and dimethyl sulfide was added. To the reaction mixture was added 0.92 g of 3,4-epoxy-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-2H-1-benzopyran dissolved in 10 ml of tetrahydrofuran. The mixture was stirred for 6 days. To the mixture were added water and a small amount of concentrated sulfuric acid. The mixture was extracted with methylene chloride and the organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) and another silica gel column chromatography (developing solution, AcOEt:hexane=1:1) to obtain 0.04 g of trans-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-4-(3-oxo-cyclopent-1-enyloxy)-2H-1-benzopyran-3-ol represented by the following formula having a melting point of 165°-167° C.

후처리

  1. additionwas added
  2. stirringThe mixture was stirred for 6 days
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe organic layer was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe resultant residue was purified

출처 및 근거

ORD 기록
ord-1fbfe959989745e5821f9fc33ddeecac
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874446

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