Hydrochloric Acid → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone

HRID 963958

반응식

HRID 963958 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+].Cl>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])[CH:33]=[CH: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 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

생성물 1

HCID 675662482'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (965 mg), benzo[b]furan-5-carbaldehyde (350 mg) and ethanol (10 ml) is added dropwise a 50% aqueous potassium hydroxide solution (2 ml), and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the solvent under reduced pressure, and to the residue are added water and diisopropyl ether. The mixture is stirred, and the aqueous layer is obtained by separation. The aqueous layer is neutralized by using a 10% hydrochloric acid under ice-cooling, and extracted with ethyl acetate. The resulting organic layer is washed with water, dried, and evaporated to remove the solvent to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone.

후처리

  1. customThe mixture is evaporated
  2. customto remove the solvent under reduced pressure
  3. additionto the residue are added water and diisopropyl ether
  4. stirringThe mixture is stirred
  5. customthe aqueous layer is obtained by separation
  6. temperaturecooling
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic layer is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent

출처 및 근거

ORD 기록
ord-40ae2288bea94fd09cf08c3d65ccf2f5
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05767094

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