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

HRID 544889Notes

Reaction equation

HRID 544889 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0a36bfbe0868476f83a030ff3e05d35d
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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