Reaktionsgleichung
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:6][C:5]2=[O:18].C([O:26][C:27]1[C:28](=[O:43])[O:29][CH:30]([CH2:40][CH2:41]O)[C:31]=1[O:32]CC1C=CC=CC=1)C1C=CC=CC=1>>[OH:26][C:27]1[C:28](=[O:43])[O:29][CH:30]([CH2:40][CH2:41][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[O:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]3=[O:18])[C:31]=1[OH:32]Komponenten
Versuchsvorschrift
Mitsunoble coupling of 0.33 g (1.4 mmol) of 6-hydroxyflavone with 0.40 g (1.17 mmol) of 3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone and subsequent benzyl group deprotection by hydrogenation were performed in a similar manner as described in the synthesis of 3,4-dihydroxy-5-[2-(4-phenoxy)phenoxyethyl]-2(5H)-furanone to provide 3,4-dihydroxy-5-[2-(flavone-6-oxy)ethyl]-2(5H)-furanone as a tan solid: mp 200-220° C. dec. (acetone/hexanes), 1H NMR (DMSO-d6) δ 8.13-7.36 (m, 8H), 7.01 (s, 1H), 4.92 (dd, 1H), 4.17 (t, 2H), 2.47-2.27 (m, 1H), 1.98-1.85 (m, 1H). 13C NMR (DMSO-d6) δ 177.23, 170.22, 162.71, 156.02, 155.36, 150.80, 132.06, 131.51, 129.42, 126.59, 124.31, 123.85, 120.49, 117.44, 106.43, 105.85, 72.24, 64.20, 31.71. Anal Calcd for C21H16O7 +0.25 H2O: C, 65.55; H, 4.44. Found: C, 65.59; H, 4.49.
Quellen und Nachweise
- ORD-Eintrag
- ord-d2566546be3243d18ebf0b56f5ad1d96
- Quelldatensatz
- uspto-grants-1999_12
- Patentnummer
- US06005000
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