Khellin → 1-(6-Hydroxy-4,7-dimethoxy-benzofuranyl)-3-(1-pyrrolidinyl)-2-buten-1-one

HRID 1278263

Reaktionsgleichung

Reaktionsgleichung von HRID 1278263
CC1[O:19][C:7]2[C:8]([O:17][CH3:18])=[C:9]3[O:16][CH:15]=[CH:14][C:10]3=[C:11]([O:12][CH3:13])[C:6]=2C(=O)C=1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[OH:19][C:7]1[CH:6]=[C:11]([O:12][CH3:13])[C:10]2[CH:14]=[C:15]([C:11](=[O:12])[CH:10]=[C:9]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:8])[O:16][C:9]=2[C:8]=1[O:17][CH3:18]

Komponenten

3

Edukt 2

HCID 3828KhellinHCID 31268Pyrrolidine

Produkt 1

HCID 542934601-(6-Hydroxy-4,7-dimethoxy-benzofuranyl)-3-(1-pyrrolidinyl)-2-buten-1-oneAusbeute 190,3 %

Versuchsvorschrift

A methanolic solution of khellin (5.2 g) and pyrrolidine (2.82 g) is heated at 80° C. for 6 hr. Upon cooling, bright orange crystals precipitate from the reaction mixture. After filtration, there is obtained 6.3 g of pure title product. Silica gel TLC Rf is 0.74 in ethyl acetate. Infrared absorptions are observed at 3180, 3160, 3120, 2300, 1630, 1600, 1530, 1345, 1325, 1260, 1170, 1155, 1140, 1130, 1060, 1050, and 1030 cm-1. NMR absorptions are observed at 7.45, 6.8, 6.25, 4.05, 3.89, 3.22-3.70, 2.68, and 1.8-2.15δ. The mass spectrum exhibits peaks at 331, 300, 261, 220, 205, 177, 111, 110, 83, and 70. The carbon:hydrogen:nitrogen ratio is 65.09:6.32:4.18.

Aufarbeitung

  1. temperatureUpon cooling
  2. custombright orange crystals precipitate from the reaction mixture
  3. filtrationAfter filtration

Quellen und Nachweise

ORD-Eintrag
ord-39077099f27843f0a179ecdbf4081ff2
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04281013

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