碘甲烷 → 5Methyl-2-trimethylsilyl-4-furaldehyde

HRID 488233

反应方程式

HRID 488233 反应方程式
[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]

参与物

6

反应物 3

HCID 6328碘甲烷HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418339正丁基锂2 次

产物 1

HCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂2 次HCID 8058正己烷溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-27849d1eb7ba4af48b9c33cd56d199c3
来源数据集
uspto-grants-1994_03
专利号
US05298633

关联笔记

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