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

HRID 2689
Notes
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Reaction equation

HRID 2689 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 (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%).

Workup

  1. customThe mixture was reacted
  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-3d0d762737d34c2080eeda70e521dbc7
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731293

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes