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

HRID 1597766

Reaction equation

HRID 1597766 reaction equation
[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

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5281417Esculin

Product 1

HCID 228840427-benzyloxy-6-D-glucosyloxycoumarinYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  1. customa reaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured into ice water
  4. filtrationThe precipitated crystals were filtered out
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-98904fd5cb18417d95f30b25c2f04850
Source dataset
uspto-grants-1998_04
Patent number
US05736522

Linked notes

Loading…