Réaction #2785

ord-3d0d762737d34c2080eeda70e521dbc7

Équation de réaction

O=c1ccc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc2o1
Esculin
ClCc1ccccc1
benzyl chloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C1COCCOCCOCCOCCOCCO1
18-crown-6-ether
[I-].[K+]
potassium iodide
→
O=c1ccc2cc(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OCc3ccccc3)cc2o1
7-benzyloxy-6-D-glucopyranosyloxycoumarin
Rendement 86.4%

Réactifs

O=c1ccc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc2o1
Esculin
ClCc1ccccc1
benzyl chloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C1COCCOCCOCCOCCOCCO1
18-crown-6-ether
[I-].[K+]
potassium iodide

Réactifs

Aucun

Solvants

CN(C)C=O
dimethylformamide

Conditions de réaction

Température
60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe mixture was reacted
  2. 2
    ConcentrationThe reaction mixture was concentrated under reduced pressure
  3. 3
    workup.ADDITIONthe residue was poured into ice water
  4. 4
    FiltrationThe precipitated crystals were filtered out
  5. 5
    Autrerecrystallized from methanol

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05731293uspto-grants-1998_03