Acetic Anhydride → HCID 19350797, compound

HRID 1636289Notes

Reaction equation

HRID 1636289 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][O:14][CH:13]([OH:16])[CH2:12][S:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][O:14][CH:13]([O:16][C:17](=[O:19])[CH3:18])[CH2:12][S:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19350843HCID 19350843, compound

Product 1

HCID 19350797HCID 19350797, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

5-Benzyloxymethyl-1,4-oxathian-2-ol (3.46 g) was dissolved in pyridine (37 ml), and the solution was cooled to 5° C. Acetic anhydride (3.27 ml) was added dropwise thereto, and the solution was stirred at the same temperature for 4 hours to complete the reaction. After removing the solvent by evaporation under reduced pressure, the residue was azeotroped with toluene to completely remove pyridine to obtain pale brown syrup. The syrup was purified on a silica gel column (eluent: n-hexane/ethyl acetate=3/1) to provide the desired product (2.94 g) as colorless syrup.

Workup

  1. customthe reaction
  2. customAfter removing the solvent
  3. customby evaporation under reduced pressure
  4. customthe residue was azeotroped with toluene to completely remove pyridine
  5. customto obtain pale brown syrup
  6. customThe syrup was purified on a silica gel column (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-746ae9b69e764118943eb7244c635a6e
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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