Acetic Anhydride → HCID 19885986, compound

HRID 654905Notes

Reaction equation

HRID 654905 reaction equation
[C:1]([O:4][CH:5]([C:14]1[CH:18]([OH:19])[O:17][C:16](=[O:20])[CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:3])[CH3:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:19][CH:18]1[O:17][C:16](=[O:20])[CH:15]=[C:14]1[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15663259HCID 15663259, compound

Product 1

HCID 19885986HCID 19885986, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(1-acetoxynonyl)-5-hydroxy-2(5H)-furanone (77.3 mg, 0.27 mmol), acetic anhydride (1/2 ml) and pyridine (1 ml) was stirred under argon at ca. 20° for 20h. After most of the solvent was removed under high vacuum (<40°), the residue was dissolved in ether (20 ml) and washed thoroughly with aqueous copper sulfate and water. Drying (magnesium sulfate) and evaporation gave a brown oil, which was flash chromatographed on silica using 30% ethyl ether/petroleum ether. Fractions with Rf 0.22 on evaporation afforded the title compound as a light yellow oil.

Workup

  1. customAfter most of the solvent was removed under high vacuum (<40°)
  2. dissolutionthe residue was dissolved in ether (20 ml)
  3. washwashed thoroughly with aqueous copper sulfate and water
  4. customDrying
  5. custom(magnesium sulfate) and evaporation
  6. customgave a brown oil, which
  7. customchromatographed on silica using 30% ethyl ether/petroleum ether
  8. customFractions with Rf 0.22 on evaporation

Sources & evidence

ORD record
ord-31ed5c4e08aa48bbad0690708630897c
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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