Methanesulfonic Acid → HCID 19930567, Verbindung

HRID 22573

Reaktionsgleichung

Reaktionsgleichung von HRID 22573
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 19930567HCID 19930567, VerbindungAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-06cee355fe944f6091fba45c9345e22f
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428177

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