Methanesulfonic Acid → 5,7-Di-tert-butyl-3-(2-methyl-dihydrobenzofuran-5-yl)benzofuran-2-one

HRID 22573노트

반응식

HRID 22573 반응식
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15]3[CH:16]=[C:17]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]=3[O:13][C:12]2=[O:28])=[CH:7][CH:6]=1)[CH:2]=C.[CH3:29]S(O)(=O)=O>C(O)(=O)C>[C:24]([C:17]1[CH:18]=[C:19]([C:20]([CH3:22])([CH3:23])[CH3:21])[C:14]2[O:13][C:12](=[O:28])[CH:11]([C:8]3[CH:7]=[CH:6][C:5]4[O:4][CH:1]([CH3:2])[CH2:29][C:10]=4[CH:9]=3)[C:15]=2[CH:16]=1)([CH3:26])([CH3:27])[CH3:25]

참가 물질

4

반응물 2

HCID 6395Methanesulfonic AcidHCID 199305653-(4-Allyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one

생성물 1

HCID 199305675,7-Di-tert-butyl-3-(2-methyl-dihydrobenzofuran-5-yl)benzofuran-2-one수율 28%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

3.80 g (10.0 mmol) of 3-(4-allyloxyphenyl)-5,7-di-tert-butyl-benzofuran-2-one are kept under nitrogen for about 4 hours at 220° C. After cooling, 10 ml of acetic acid and 0.3 ml of methanesulfonic acid are added and the reaction mixture is refluxed for 7 hours. After dilution with 100 ml of water, the product is extracted with dichloromethane. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue on silica gel with the eluant system dichloromethane/hexane=1:2 and crystallisation of the pure fractions from ligroin gives 1.07 g (28%)of 5,7-di-tert-butyl-3-(2-methyl-dihydrobenzofuran-5-yl)benzofuran-2-one, m.p. 136°-152° C. as a mixture of diastereoisomers (compound (101), Table 1).

후처리

  1. temperatureAfter cooling
  2. temperaturethe reaction mixture is refluxed for 7 hours
  3. extractionAfter dilution with 100 ml of water, the product is extracted with dichloromethane
  4. washThe organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator
  7. customChromatography of the residue on silica gel with the eluant system dichloromethane/hexane=1:2 and crystallisation of the pure fractions from ligroin

출처 및 근거

ORD 기록
ord-06cee355fe944f6091fba45c9345e22f
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428177

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