Acetic Anhydride → 3,5-Dioxohexanoic acid

HRID 2360543Notes

Reaction equation

HRID 2360543 reaction equation
N([C@@H]1[C@@H:11]([OH:12])[C@H:10](O)[C@@H:9]([CH2:14]O)[O:8][C@H]1SC)=[N+]=[N-].C([O:19][C:20](=[O:22])[CH3:21])(=O)C>N1C=CC=CC=1>[CH3:14][C:9]([CH2:10][C:11]([CH2:21][C:20]([OH:19])=[O:22])=[O:12])=[O:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9794681HCID 9794681, compound

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To methyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside. (10 g, 42.50 mmol) in pyridine (50 mL) at 0° C. was added acetic anhydride (20 g) and the reaction stirred for 1 hour. The reaction mixture was evaporated to dryness and the residue extracted to give the title triacetate (15.23 g, quantitative), Rf=0.7 (CHCl3/Petroleum ethers, 1:1).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionthe residue extracted

Sources & evidence

ORD record
ord-467f845c277b4daaa537ebfdccd1ce31
Source dataset
uspto-grants-2014_04
Patent number
US08686131B2

Reaction notes

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