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Water → D-Glucitol, 1,5-anhydro-1-C-[5-(2-azulenylmethyl)-2-hydroxyphenyl]-, (1S)-

HRID 1376006
Notes
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Reaction equation

HRID 1376006 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C1(OC)C=CC=CC=1.[CH:13]1[C:22]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:14]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:69]CC2C=CC=CC=2)=[C:28]([C@@H:30]2[O:59][C@H:58]([CH2:60][O:61]CC3C=CC=CC=3)[C@@H:49]([O:50]CC3C=CC=CC=3)[C@H:40]([O:41]CC3C=CC=CC=3)[C@H:31]2[O:32]CC2C=CC=CC=2)[CH:29]=1.O>C(Cl)Cl>[CH:13]1[C:22]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:14]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:69])=[C:28]([C@@H:30]2[O:59][C@H:58]([CH2:60][OH:61])[C@@H:49]([OH:50])[C@H:40]([OH:41])[C@H:31]2[OH:32])[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 11535213HCID 11535213, compound

Product 1

HCID 11560307D-Glucitol, 1,5-anhydro-1-C-[5-(2-azulenylmethyl)-2-hydroxyphenyl]-, (1S)-Yield 30.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Aluminum chloride (0.12 g) and anisole (4.0 ml) were added to a solution of (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-(benzyloxy)phenyl]-2,3,4,6-tetra-O-benzyl-D-glucitol (0.07 g) in methylene chloride (5 ml) and the mixture was stirred at room temperature for two hours. 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-hydroxyphenyl]-D-glucitol (0.01 g).

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-4f37995bf11d4aff81cb68901685cf40
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169761B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes