咪唑 → Tert-butyldimethyl(4-((trimethylsilyl)ethynyl)benzyloxy)silane

HRID 2405645

反应方程式

HRID 2405645 反应方程式
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1)([CH3:4])[CH3:3].N1C=CN=C1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[C:21]([Si:24]([CH3:26])([CH3:25])[O:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])=[CH:12][CH:11]=1)([CH3:23])([CH3:22])[CH3:20]

参与物

6

反应物 4

HCID 795咪唑HCID 24083Sulfuric acid magnesium salt (1:1)HCID 28928叔丁基二甲基氯硅烷HCID 112411654-(三甲基硅基乙炔基)苄基甲醇

产物 1

HCID 59417152Tert-butyldimethyl(4-((trimethylsilyl)ethynyl)benzyloxy)silane收率 95.2%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
0 °C

实验过程

Under argon condition, (4-((trimethylsilyl)ethynyl)phenyl) methanol (258 mg, 1.26 mmol) was dissolved in 5 mL of dry THF and then cooled to 0° C., and imidazole (103 mg, 1.52 mmol) and TBSCl (228 mg, 1.52 mmol) dissolved in 3 mL of dry THF were added thereto. Thereafter, the temperature was raised to room temperature, and the reaction mixture was stirred for 15 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (10 mL×4), and the organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 383 mg (1.20 mmol, 95%) of the desired compound.

后处理

  1. additionwere added
  2. temperatureThereafter, the temperature was raised to room temperature
  3. customUpon completion of the reaction
  4. customthe reaction was terminated
  5. additionby adding 10 mL of aqueous saturated ammonium chloride solution
  6. extractionThe reaction mixture was extracted with ethyl acetate (10 mL×4)
  7. customthe organic layer thus obtained
  8. customto remove water
  9. filtrationThe precipitate was filtered out
  10. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  11. custompurified by column chromatography

来源与证据

ORD记录
ord-0f081623c6de4112b4767f864969c0ef
来源数据集
uspto-grants-2014_08
专利号
US08809012B2

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