三甲基氯硅烷 → 1-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 2816

反应方程式

HRID 2816 反应方程式
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[C:17]([C:20]1[CH:24]=[C:23]([CH3:25])[O:22][C:21]=1[CH3:26])(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:26][C:21]1[O:22][C:23]([CH3:25])=[CH:24][C:20]=1[C:17]([C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])([OH:19])[CH3:18]

参与物

7

反应物 5

HCID 6397三甲基氯硅烷HCID 127484-甲基噻唑HCID 615273-乙酰基-2,5-二甲基呋喃HCID 516892碳酸氢钠HCID 178418339正丁基锂2 次

产物 1

HCID 189362891-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
-70 °C

实验过程

4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C.

后处理

  1. temperatureto warm to room temperature
  2. temperatureAfter 30 minutes the mixture was again cooled to -70° C.
  3. temperatureto warm to room temperature
  4. waitAfter 30 minutes
  5. extractionthe mixture was extracted with diethylether
  6. washThe combined extracts were washed
  7. customdried
  8. customevaporated

来源与证据

ORD记录
ord-01df543a66bb4268b36a7edbe14246e3
来源数据集
uspto-grants-1998_03
专利号
US05731335

关联笔记

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