Ethanol → 4,6-dichloro-1-(beta-D-glucopyranosyl)indoline

HRID 544889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544889
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.[O:12]=[CH:13][C@@H:14]([C@H:16]([C@@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[OH:17])O.C(O)C>O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C@@H:22]1[O:23][C@H:14]([CH2:13][OH:12])[C@@H:16]([OH:17])[C@H:18]([OH:19])[C@H:20]1[OH:21]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 162444484,6-Dichloroindoline

Produkt 1

HCID 671990964,6-dichloro-1-(beta-D-glucopyranosyl)indoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloroindoline (6.57 g) and D-glucose (10.70 g) in H2O (25 ml)-ethyl alcohol (160 ml) was refluxed for 3 days. The organic solvent was evaporated under reduced pressure, and thereto were added brine and ammonium sulfate. The mixture was extracted with ethyl acetate 5 times, and the combined organic layer was dried over sodium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure to give crude 4,6-dichloro-1-(β-D-gluco-pyranosyl)indoline, which was used in the subsequent step without further purification.

Aufarbeitung

  1. temperaturewas refluxed for 3 days
  2. customThe organic solvent was evaporated under reduced pressure
  3. additionwere added brine and ammonium sulfate
  4. extractionThe mixture was extracted with ethyl acetate 5 times
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. filtrationThe insoluble materials were filtered off
  7. customthe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0a36bfbe0868476f83a030ff3e05d35d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935674B2

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