Methyl iodide → 5Methyl-2-trimethylsilyl-4-furaldehyde

HRID 326358

Reaktionsgleichung

Reaktionsgleichung von HRID 326358
[CH2:1]([Li])CCC.[CH3:6][Si:7]([CH3:16])([CH3:15])[C:8]1[O:9][CH:10]=[C:11]([CH:13]=[O:14])[CH:12]=1.IC>CCCCCC.O1CCCC1>[CH3:1][C:10]1[O:9][C:8]([Si:7]([CH3:16])([CH3:15])[CH3:6])=[CH:12][C:11]=1[CH:13]=[O:14]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418339Butyllithium2×

Produkt 1

HCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

n-Butyl lithium (a 1.6M solution in hexane; 2.04 ml, 3.28 mmol) was added dropwise to a solution of N,N'N'-trimethylethylenediamine (0.46 ml, 3.56 mmol) in tetrahydrofuran (7 ml) at -78 degrees under argon. After 15 minutes, a solution of 2-trimethylsilyl-4-furaldehyde (0.5 g, 2.98 mmol) in tetrahydrofuran (2 ml) was added, followed by n-butyl lithium (3.72 ml, 5.94 mmol) after 15 minutes. Iodomethane (1.12 ml, 17.9 mmol) was then added and the mixture was allowed to warm to room temperature gradually over 1/2 hour. The mixture was quenched with brine and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by flash chromatography using 10% ethyl ether/hexane. Fractions with Rf of about 0.22 on evaporation afforded the title methylfuran as a light yellow oil.

Aufarbeitung

  1. customThe mixture was quenched with brine
  2. extractionextracted with ethyl ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by flash chromatography
  7. customFractions with Rf of about 0.22 on evaporation

Quellen und Nachweise

ORD-Eintrag
ord-c7b1b100efeb4ab192a283dbeecb363c
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05268387

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