Potassium Hydroxide → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone

HRID 355344

반응식

HRID 355344 반응식
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.[OH-].[K+]>[Pt].C(O)C>[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][CH:39]=[CH: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]

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

생성물 1

HCID 99331252'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone수율 71.1%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 702Ethanol용매

실험 절차

To a mixture of 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (1500 mg), benzo[b]furan-5-carbaldehyde (545 mg) and ethanol (15 ml) is added dropwise a 50% aqueous potassium hydroxide solution (3 ml), and the mixture is stirred at room temperature overnight. The mixture is subjected to catalytic hydrogenation by using as a catalyst 10% platinum on activated carbon (303 mg) under atmospheric pressure. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. To the residue are added toluene and water, and the mixture is stirred. The aqueous layer is collected by filtration, acidified with a 10% hydrochloric acid under ice-cooling, and extracted with ethyl acetate. The obtained organic layer is washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography to give 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone (982 mg). The physical properties of this product are the same as those of the compound of Example 1.

후처리

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionTo the residue are added toluene and water
  4. stirringthe mixture is stirred
  5. filtrationThe aqueous layer is collected by filtration
  6. temperaturecooling
  7. extractionextracted with ethyl acetate
  8. washThe obtained organic layer is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent
  12. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f2df04d9bc2e49b4aa4085cac72b5dba
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830873

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