碘甲烷 → 2-Methyl-4-phenyl-3-furaldehyde

HRID 326366

反应方程式

HRID 326366 反应方程式
[CH2:1]([Li])CCC.CNCCN(C)C.[C:13]1([C:19]2[C:20]([CH:24]=[O:25])=[CH:21][O:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.IC>CCCCCC.O1CCCC1>[CH3:1][C:21]1[O:22][CH:23]=[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]=1[CH:24]=[O:25]

参与物

7

反应物 4

HCID 6328碘甲烷HCID 67338N,N,N'-三甲基乙二胺HCID 150371484-Phenyl-3-furaldehydeHCID 178418339正丁基锂2 次

产物 1

HCID 150371592-Methyl-4-phenyl-3-furaldehyde

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂HCID 8058正己烷溶剂2 次

实验过程

n-Butyllithium (a 1.6m solution in hexane, 2.43 ml, 3.89 mmol) was added to a solution of trimethylethylenediamine (397 mg, 3.89 mmol) in tetrahydrofuran (25 ml) at 0 degrees under argon. After 20 minutes the solution was cooled to -78 degres and 4-phenyl-3-furaldehyde (608 mg, 3.35 mmol) was added. This mixture was allowed to gradually warm to -20 degrees and stirred for 11/2 hours, then recooled to -78 degrees before n-butyllithium (a 1.6M solution in hexane, 2.43 ml, 3.89 mmol) was added dropwise. The stirring mixture was again gradually warmed to -20 degrees and stirred for 2 hours before iodomethane (2.56 g 17.67 mmol) was added. After stirring for 18 hours at -20 degrees the reaction was quenched with ice-cold 10% (v/v) hydrochloric acid and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 20% ethyl ether/hexanes to give the title aldehyde.

后处理

  1. additionwas added
  2. temperatureto gradually warm to -20 degrees
  3. additionwas added dropwise
  4. temperatureThe stirring mixture was again gradually warmed to -20 degrees
  5. additionwas added
  6. stirringAfter stirring for 18 hours at -20 degrees the reaction
  7. customwas quenched with ice-cold 10% (v/v) hydrochloric acid
  8. extractionthe organics were extracted into ethyl ether
  9. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
  10. customEvaporation of the
  11. dry with materialdried (magnesium sulfate)
  12. customextracts gave an oil which
  13. customwas purified by flash chromatography on silica using 20% ethyl ether/hexanes

来源与证据

ORD记录
ord-4905bc23f6ca4ea7b240873898cccace
来源数据集
uspto-grants-1993_12
专利号
US05268387

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