Ethanol → 3-(3,4-dihydroxycinnamoylamino)-4-(2-methylphenyl)-7,8-dihydrocyclopenta[g][1]benzopyran-2(6H)-one

HRID 258033

Reaktionsgleichung

Reaktionsgleichung von HRID 258033
C[O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[O:35]C)[CH:6]=[CH:7][C:8]([NH:10][C:11]1[C:12](=[O:31])[O:13][C:14]2[CH:27]=[C:26]3[CH2:28][CH2:29][CH2:30][C:25]3=[CH:24][C:15]=2[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[O:9].[B].C(O)C>ClCCl.O>[OH:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[OH:35])[CH:6]=[CH:7][C:8]([NH:10][C:11]1[C:12](=[O:31])[O:13][C:14]2[CH:27]=[C:26]3[CH2:28][CH2:29][CH2:30][C:25]3=[CH:24][C:15]=2[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[O:9]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 5462311BoronHCID 540029353-(3,4-dimethoxycinnamoylamino)-4-(2-methylphenyl)-7,8-dihydrocylopenta[g][1]benzopyran-2(6H)-one

Produkt 1

HCID 544186493-(3,4-dihydroxycinnamoylamino)-4-(2-methylphenyl)-7,8-dihydrocyclopenta[g][1]benzopyran-2(6H)-oneAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(3,4-dimethoxycinnamoylamino)-4-(2-methylphenyl)-7,8-dihydrocylopenta[g][1]benzopyran-2(6H)-one (400 mg) in dichloromethane (6 ml) was added boron tribromidedichloromethane (1:2, 1 ml) dropwise with ice-cooling and stirring. The mixture was further stirred under ice-cooling for 1 hour and, then, added gradually to ethanol (5 ml) with ice-cooling. The mixture was diluted with water and extracted with ethyl acetate, the extract was washed with water and dried (MgSO4), and the solvent was distilled off to give crystals of 3-(3,4-dihydroxycinnamoylamino)-4-(2-methylphenyl)-7,8-dihydrocyclopenta[g][1]benzopyran-2(6H)-one (361 mg, 95.8%). Recrystallization from ethanol gave light brown prisms, m.p. 295°-297° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was further stirred under ice-
  3. temperaturecooling for 1 hour
  4. temperaturecooling
  5. extractionextracted with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-64670c680b504972ae9d8d20c870dae7
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264454

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