1-Benzofuran-5-carbaldehyde → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(2,3-dihydro-5-benzo[b]furanyl)propiophenone

HRID 355345

Reaction equation

HRID 355345 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=1[C:32](=[O:34])[CH3:33])(=O)C.[O:35]1[CH:39]=[CH:38][C:37]2[CH:40]=[C:41]([CH:44]=O)[CH:42]=[CH:43][C:36]1=2>C(O)C.C(O)(=O)C.[C].[Pd]>[C@@H:6]1([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=2[C:32](=[O:34])[CH2:33][CH2:44][C:41]2[CH:42]=[CH:43][C:36]3[O:35][CH2:39][CH2:38][C:37]=3[CH:40]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

6

Reactant 2

HCID 27738751-Benzofuran-5-carbaldehydeHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

Product 1

HCID 117976222'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(2,3-dihydro-5-benzo[b]furanyl)propiophenoneYield 78.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

2'-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (1268 mg) and benzo[b]furan-5-carbaldehyde (911 mg) are treated in the same manner as in Example 1 to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone. This product is dissolved in a mixture of ethanol (20 ml) and acetic acid (2 ml), and the mixture is subjected to catalytic hydrogenation by using 10% palladium-carbon (0.5 g) under atmospheric pressure. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. To the residue are added ethyl acetate and water, and the mixture is stirred. The organic layer is collected, washed with a saturated aqueous sodium hydrogen carbonate solution, dried, and evaporated to remove the solvent. The residue is pulverized with chloroform-diisopropyl ether, and the obtained powder is collected by filtration and dried to give 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(2,3-dihydro-5-benzo[b]furanyl)propiophenone (920 mg).

Workup

  1. customto give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. additionTo the residue are added ethyl acetate and water
  5. customThe organic layer is collected
  6. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. filtrationthe obtained powder is collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-628431c8253e4dfcbc37107b1f46b615
Source dataset
uspto-grants-1998_11
Patent number
US05830873

Linked notes

Loading…