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

HRID 1597766

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 [VIII] (1.0 g), benzyl chloride (1.0 g), potassium carbonate (0.7 g), a catalytic amount of 18-crown-6-ether and potassium iodide, and dimethylformamide (40 ml) were added to an eggplant-shaped flask (100 ml). The mixture was stirred at 60° C. for 8 hours to cause a reaction. 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-glucosyloxycoumarin (VII-1) (melting point=184° to 186° C, mass spectrum (M+)=430, yield =86.4%).

Aufarbeitung

customa reaction
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-98904fd5cb18417d95f30b25c2f04850
Quelldatensatz: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05736522

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