三乙基氯硅烷 → 3-Phenyl-2-triethylsilyl-4furaldehyde

HRID 273962

反应方程式

HRID 273962 反应方程式
C([Li])CCC.CN1CCNCC1.[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.C([Li])(CC)C.Cl[Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34]>CCCCCC.O1CCCC1.C1CCCCC1>[C:13]1([C:19]2[C:20]([CH:24]=[O:25])=[CH:21][O:22][C:23]=2[Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参与物

9

反应物 5

HCID 13819三乙基氯硅烷HCID 53167N-甲基哌嗪HCID 150371484-Phenyl-3-furaldehydeHCID 178418339正丁基锂HCID 178418400仲丁基锂

产物 1

HCID 150371493-Phenyl-2-triethylsilyl-4furaldehyde

试剂、催化剂与溶剂 3

HCID 8028四氢呋喃溶剂HCID 8058正己烷溶剂HCID 8078环己烷溶剂

实验过程

n-Butyllithium (a 1.42M solution in hexane, 2.33 ml, 3.31 mmol) was added to a solution of 1-methylpiperazine (331 mg. 3.31 mmol) in tetrahydrofuran (15 ml) at 0 degrees under argon. After 15 minutes the solution was cooled to -78 degrees and 4-phenyl-3-furaldehyde (517 mg, 3.01 mmol) was added. This mixture was warmed to 0 degrees and stirred for 15 minutes, then recooled to -78 degrees before sec-butyllithium (a 1.3M solution in cyclohexane, 2.77 ml, 3.61 mmol) was added dropwise. This solution was stirred 12 hours at -78 degrees C. before chlorotriethylsilane (1.81 g, 12.02 mmol) was added. The mixture was allowed to warm gradually to room temperature and stirred an additional 11/2 hours. The reaction was quenched with ice-cold 5% (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 10% ethyl acetate/hexanes to give the title aldehyde.

后处理

  1. temperatureAfter 15 minutes the solution was cooled to -78 degrees
  2. temperatureThis mixture was warmed to 0 degrees
  3. additionwas added dropwise
  4. stirringThis solution was stirred 12 hours at -78 degrees C
  5. stirringstirred an additional 11/2 hours
  6. customThe reaction was quenched with ice-cold 5% (V/V) hydrochloric acid
  7. extractionthe organics were extracted into ethyl ether
  8. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
  9. customEvaporation of the
  10. dry with materialdried (magnesium sulfate)
  11. customextracts gave an oil which
  12. customwas purified by flash chromatography on silica using 10% ethyl acetate/hexanes

来源与证据

ORD记录
ord-10d73349a7664917a2998a5e8a0a4ab0
来源数据集
uspto-grants-1995_02
专利号
US05387606

关联笔记

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