Hydrochloric Acid → HCID 58786178, compound

HRID 1376000Notes

Reaction equation

HRID 1376000 reaction equation
Cl.[CH:2]1[C:11]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:4][C:3]=1[CH2:12][C:13]1[C:14]([O:44][CH3:45])=[CH:15][C:16]([O:42][CH3:43])=[C:17]([C@@H:19]2[O:36][C@H:35]([CH2:37][O:38]COC)[C@@H:30]([O:31]COC)[C@H:25]([O:26]COC)[C@H:20]2[O:21]COC)[CH:18]=1.O>CO>[CH:2]1[C:11]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:4][C:3]=1[CH2:12][C:13]1[C:14]([O:44][CH3:45])=[CH:15][C:16]([O:42][CH3:43])=[C:17]([C@@H:19]2[O:36][C@H:35]([CH2:37][OH:38])[C@@H:30]([OH:31])[C@H:25]([OH:26])[C@H:20]2[OH:21])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58786246HCID 58786246, compound

Product 1

HCID 58786178HCID 58786178, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10% aqueous solution of hydrochloric acid (0.5 ml) was added to a solution of (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2,4-dimethoxyphenyl]-2,3,4,6-tetrakis-O-(methoxymethyl)-D-glucitol (0.09 g) in methanol (2.0 ml) and the mixture was refluxed with heating for 30 minutes. The reaction mixture was poured into ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2,4-dimethoxyphenyl]-D-glucitol (0.02 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 30 minutes
  3. additionThe reaction mixture was poured into ice-
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  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 (chloroform-methanol)

Sources & evidence

ORD record
ord-1f5e5e9e6eb14deda31fd813cdba1d2e
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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