Acetic Anhydride → HCID 58786162, compound

HRID 1375996Notes

Reaction equation

HRID 1375996 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH:8]1[C:17]2[C:11]([CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:10][C:9]=1[CH2:18][C:19]1[CH:20]=[C:21]([C@@H:25]2[O:33][C@H:32]([CH2:34][OH:35])[C@@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]2[OH:27])[CH:22]=[CH:23][CH:24]=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:26]([O:27][C@@H:26]1[C@@H:28]([O:29][C:28](=[O:29])[CH3:30])[C@H:30]([O:31][C:32](=[O:33])[CH3:34])[C@@H:32]([CH2:34][O:35][C:5](=[O:7])[CH3:6])[O:33][C@H:25]1[C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([CH2:18][C:9]2[CH:10]=[C:11]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=[CH:12]3)[CH:8]=2)[CH:20]=1)(=[O:27])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 9886174HCID 9886174, compound

Product 1

HCID 58786162HCID 58786162, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (0.3 ml) was added to a solution of (1S)-1,5-anhydro-1-[3-(azulen-2-ylmethyl)phenyl]-D-glucitol (0.24 g) in pyridine (5.0 ml) at room temperature and the mixture was stirred for 15 hours. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with 10% aqueous solution of hydrochloric acid, 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 (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-(azulen-2-ylmethyl)phenyl]-D-glucitol (0.34 g).

Workup

  1. washThe diluted solution was washed with 10% aqueous solution of hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate, and saturated brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d4c6de2425dd443e979d44c33937fb25
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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