Potassium Iodide → 7-benzyloxy-6-D-glucosyloxycoumarin

HRID 2689

Reaktionsgleichung

[CH:1]1[C:6]([O:7][C@@H:8]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]2[OH:18])=[C:5]([OH:19])[CH:4]=[C:3]2[O:20][C:21]([CH:23]=[CH:24][C:2]=12)=[O:22].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+]>CN(C)C=O>[CH2:25]([O:19][C:5]1[CH:4]=[C:3]2[C:2]([CH:24]=[CH:23][C:21](=[O:22])[O:20]2)=[CH:1][C:6]=1[O:7][CH:8]1[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]1[OH:18])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Esculin (1.0 g), benzyl chloride (1.0 g), potassium carbonate (0.7 g), catalytic amounts of 18-crown-6-ether and potassium iodide, and dimethylformamide (40 ml) were placed in an eggplant-shaped flask (100 ml). The mixture was reacted while stirred at 60° C. for 8 hours. The reaction mixture was concentrated under reduced pressure and the residue was poured into ice water. The precipitated crystals were filtered out and recrystallized from methanol to obtain 7-benzyloxy-6-D-glucopyranosyloxycoumarin (VIII-2) (melting point=184° to 186° C., mass spectrum (M+)=430, yield=86.4%).

Aufarbeitung

customThe mixture was reacted
concentrationThe reaction mixture was concentrated under reduced pressure
additionthe residue was poured into ice water
filtrationThe precipitated crystals were filtered out
customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag: ord-3d0d762737d34c2080eeda70e521dbc7
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05731293

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