Hydrochloric Acid → 4-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[(E)-2-(4-bromophenyl)vinyl]benzofuran

HRID 230927노트

반응식

HRID 230927 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32]C(OC)=O)[C:26]=1[C:37](=O)[CH3:38])(=[O:3])[CH3:2].[Br:40][C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=1.[OH-].[K+].Cl>C(O)C.O>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:26]2[C:37](/[CH:38]=[CH:45]/[C:44]3[CH:47]=[CH:48][C:41]([Br:40])=[CH:42][CH:43]=3)=[CH:32][O:31][C:27]=2[CH:28]=[CH:29][CH:30]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 707414-BromobenzaldehydeHCID 671359432'-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-(methoxycarbonylmethoxy)acetophenone

생성물 1

HCID 671363394-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[(E)-2-(4-bromophenyl)vinyl]benzofuran수율 31.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a suspension of 2′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6′-(methoxycarbonylmethoxy)acetophenone (0.55 g) and 4-bromobenzaldehyde (0.19 g) in ethanol (9 mL) were added water (3 mL) and potassium hydroxide (0.67 g), and the mixture was stirred at room temperature for three days. To the reaction mixture was added 2 mol/L hydrochloric acid (7 mL), and the resulting mixture was extracted with ethyl acetate twice. The extracts were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. To the residue were added sodium acetate (1.97 g), acetic acid (5 mL) and acetic anhydride (2.08 mL), and the mixture was stirred at 115° C. overnight. The reaction mixture was cooled to room temperature and poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2) to give the title compound (0.2 g).

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate twice
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. additionTo the residue were added sodium acetate (1.97 g), acetic acid (5 mL) and acetic anhydride (2.08 mL)
  5. stirringthe mixture was stirred at 115° C. overnight
  6. temperatureThe reaction mixture was cooled to room temperature
  7. additionpoured into water
  8. extractionthe resulting mixture was extracted with ethyl acetate
  9. washThe extract was washed with water and brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed under reduced pressure
  12. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2)

출처 및 근거

ORD 기록
ord-0de56be5cfec4e798beef56d98a833d1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566699B2

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