Acetic Anhydride → 4-(1-Acetoxytridecyl)-2-trimethylsilylfuran

HRID 654910Notes

Reaction equation

HRID 654910 reaction equation
[OH:1][CH:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([O:1][CH:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuran

Product 1

HCID 156632554-(1-Acetoxytridecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (1.32 g, 3.89 mmol), acetic anhydride (4 ml) and pyridine (6 ml) was stirred under argon at ca. 20° for 16 h. After most of the solvent was removed under high vacuum (<40°), the residue was dissolved in ethyl 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 0.55 (10% ethyl ether/petroleum ether) on evaporation gave the desired trimethylsilylfuran as a pale yellow oil.

Workup

  1. customAfter most of the solvent was removed under high vacuum (<40°)
  2. dissolutionthe residue was dissolved in ethyl 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 0.55 (10% ethyl ether/petroleum ether) on evaporation

Sources & evidence

ORD record
ord-7596f8836ea94aa88a907baddf772f73
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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