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

HRID 963958

反応式

HRID 963958 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-40ae2288bea94fd09cf08c3d65ccf2f5
出典データセット
uspto-grants-1998_06
特許番号
US05767094

関連ノート

読み込み中…