Acetic Anhydride → HCID 15723360, compound

HRID 654908Notes

Reaction equation

HRID 654908 reaction equation
[OH:1][CH:2]([C:13]1[CH:14]=[C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])[O:16][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:1][CH:2]([C:13]1[CH:14]=[C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])[O:16][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 198858964-(1-Hydroxyundecyl)-2-trimethylsilylfuran

Product 1

HCID 15723360HCID 15723360, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(1-hydroxyundecyl)-2-trimethylsilylfuran (1.21 g, 3.89 mmol), acetic anhydride (4 ml) and pyridine (6 ml) was stirred under argon at ca. 20° for 14h. After most of the solvent was removed under high vacuum (<40°), 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 of about 0.3 on evaporation afforded the captioned compound as a pale yellow oil.

Workup

  1. customAfter most of the solvent was removed under high vacuum (<40°)
  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 of about 0.3 on evaporation

Sources & evidence

ORD record
ord-f54219dae3b040bba35494a3f323ba51
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…