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

HRID 273950

반응식

HRID 273950 반응식
[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]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418339Butyllithium2회

생성물 1

HCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2fc87ac0d97f411c83c6462c5543ed1c
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387606

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