Hydrochloric Acid → HCID 58786150, compound

HRID 1375997Notes

Reaction equation

HRID 1375997 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:11][C@H:10]1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][C:35]2[CH:44]=[C:43]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=[CH:42]3)[CH:36]=2)[CH:29]=1)(=[O:7])[CH3:6].[C:45](OC(=O)C)(=[O:47])[CH3:46].Cl>C(Cl)Cl>[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:11][C@H:10]1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][C:35]2[CH:36]=[C:37]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=[CH:38]3)[C:44]=2[C:45](=[O:47])[CH3:46])[CH:29]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 58786162HCID 58786162, compound

Product 1

HCID 58786150HCID 58786150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (0.24 g) was added to a solution of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-(azulen-2-ylmethyl)phenyl]-D-glucitol (0.20 g) in methylene chloride (20 ml) at 0° C. and the mixture was stirred for 30 minutes. Next, acetic anhydride (0.17 ml) was added dropwise to the reaction mixture at 0° C. and the mixture was refluxed with stirring for 30 minutes and further 16 hours. The reaction mixture was added to 10% aqueous solution of hydrochloric acid under cooling with ice and was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated brine in that order and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (2S,3S,4R,5R,6R)-2-[3-[(1-acetylazulen-2-yl)methyl]phenyl]-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.09 g).

Workup

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for 30 minutes and further 16 hours
  3. temperatureunder cooling with ice
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cc61ad9f17ff4c6c817329b89533baa2
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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