Dichloromethane → HCID 19020981, Verbindung

HRID 1109643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109643
ClCCl.FC(F)(F)C(O)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:23][CH:24]2[CH:29]([CH2:30][C:31]3[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=3)[CH2:28][O:27][C:25]2=[O:26])[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20]>C(OCC)(=O)C>[CH3:42][O:41][C:33]1[C:34]([O:39][CH3:40])=[C:35]([O:37][CH3:38])[C:36]2[C:14]3[C:13]([O:12][CH3:11])=[C:18]([O:19][CH3:20])[C:17]([O:21][CH3:22])=[CH:16][C:15]=3[CH2:23][CH:24]3[C:25](=[O:26])[O:27][CH2:28][CH:29]3[CH2:30][C:31]=2[CH:32]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 99810053,4-Bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one

Produkt 1

HCID 19020981HCID 19020981, VerbindungAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolved in a mixture consisting of 0.5 ml of dichloromethane and 0.05 ml of trifluoroacetic acid were 50 mg (0.112 mmol) of 2,3-bis[1-(3,4,5-trimethoxyphenyl)methyl]butanolide. The solution was added with 150 mg (0.32 mmol) of ferric perchlorate, followed by stirring at room temperature for 19 hours. The reaction mixture was dissolved in 10 ml of ethyl acetate. The resulting solution was washed successively with 2N-HCl, water and saturated NaHCO3. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby colorless oil was obtained. The oil was purified by thinlayer chromatography (TLC) (silica gel: "MERCK #5744", eluent: 1:3 mixed solvent of acetone and hexane), whereby 28.5 mg of the title compound were obtained as a colorless solid (yield: 57%).

Aufarbeitung

  1. dissolutionDissolved in a mixture
  2. washThe resulting solution was washed successively with 2N-HCl, water and saturated NaHCO3
  3. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, whereby colorless oil
  5. customwas obtained
  6. customThe oil was purified by thinlayer chromatography (TLC) (silica gel: "MERCK #5744", eluent: 1:3 mixed solvent of acetone and hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a316d44c00d04860b3683075bcb36c7d
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05321135

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