Acetic Anhydride → HCID 15723359, compound

HRID 727951Notes

Reaction equation

HRID 727951 reaction equation
[OH:1][CH:2]([C:11]1[CH:12]=[C:13]([Si:16]([CH3:19])([CH3:18])[CH3:17])[O:14][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:1][CH:2]([C:11]1[CH:12]=[C:13]([Si:16]([CH3:19])([CH3:18])[CH3:17])[O:14][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 157287174-(1-Hydroxynonyl)-2-trimethylsilylfuran

Product 1

HCID 15723359HCID 15723359, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(1-hydroxynonyl)-2-trimethylsilylfuran (1.65 g, 5.9 mmol), acetic anhydride (2 ml) and pyridine (3 ml) was stirred under argon at approximately 20° for 17 hours. After most of the solvent was removed under high vacuum (less than 40° C.), the residue was dissolved in ether (40 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 5% ethyl ether/petroleum ether. Fractions with Rf 0.32 on evaporation afforded 4-(1-acetoxynonyl)-2-trimethylsilylfuran as a pale yellow oil.

Workup

  1. customAfter most of the solvent was removed under high vacuum (less than 40° C.)
  2. dissolutionthe residue was dissolved in ether (40 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 5% ethyl ether/petroleum ether
  8. customFractions with Rf 0.32 on evaporation

Sources & evidence

ORD record
ord-afc2e5a9fcb84fb69135eb043b5c47e0
Source dataset
uspto-grants-1991_09
Patent number
US05045564

Reaction notes

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