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

HRID 488233

Reaction equation

HRID 488233 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (a 1.6 M 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.

Workup

  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

Sources & evidence

ORD record
ord-27849d1eb7ba4af48b9c33cd56d199c3
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Linked notes

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