Citric Acid → HCID 10792589, compound

HRID 1003938Notes

Reaction equation

HRID 1003938 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([OH:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[O:22][C@@H:23]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]3[OH:25])=[O:13])[CH:8]=[CH:9][C:2]1=2.C(N(CC)CC)C.[C:41](Cl)(=[O:43])[CH3:42].C(O)(=O)[CH2:46][C:47](CC(O)=O)(C(O)=O)[OH:48]>CN(C)C(=O)C>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][C:41](=[O:43])[CH3:42])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[O:22][C@@H:23]3[O:31][C@H:30]([CH2:32][O:33][C:47](=[O:48])[CH3:46])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]3[OH:25])=[O:13])[CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 6918439209746-56-5

Product 1

HCID 10792589HCID 10792589, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (500 mg) is dissolved in N,N-dimethylacetamide (3.5 ml), and thereto is added triethylamine (315 mg). To the mixture is added dropwise acetyl chloride (282 mg) under ice-cooling, and the mixture is stirred under ice-cooling for 30 minutes, and stirred at room temperature overnight. The reaction mixture is poured into chilled 10% aqueous citric acid solution, and extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]-furanyl)-2'-(6-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-4'-methylpropiophenone (304 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringstirred at room temperature overnight
  4. additionThe reaction mixture is poured
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-62e821b465464fa2878e9adefd2f4229
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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