Acetic Anhydride → HCID 19885903, compound

HRID 654920Notes

Reaction equation

HRID 654920 reaction equation
[OH:1][CH:2]([C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([O:1][CH:2]([C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19885922HCID 19885922, compound

Product 1

HCID 19885903HCID 19885903, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A solution of 3-(1-hydroxy-4-phenylbutyl)-furan (0.167 g., 0.772 mmol), acetic anhydride (1 ml, excess) and pyridine (3 to 4 drops, excess), was stirred at room temperature until no starting material remained (as monitored by TLC). The reaction mixture was then partitioned between ethyl ether and a 5% ammonium chloride solution. The organic portion was washed repeatedly with saturated sodium bicarbonate solution, aqueous cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give 3-(1-acetoxy-4-phenylbutyl)furan.

Workup

  1. customThe reaction mixture was then partitioned between ethyl ether
  2. washThe organic portion was washed repeatedly with saturated sodium bicarbonate solution, aqueous cupric sulfate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ad5b736df88447489e7120d6c0b09d39
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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