4-[(三甲基硅基)乙炔基]苯甲酸甲酯 → 4-(三甲基硅基乙炔基)苄基甲醇

HRID 2405663

反应方程式

HRID 2405663 反应方程式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:13][Si:12]([C:11]#[C:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1)([CH3:14])[CH3:15]

参与物

4

反应物 2

HCID 6401614-[(三甲基硅基)乙炔基]苯甲酸甲酯HCID 21226445Aluminium lithium hydride

产物 1

HCID 112411654-(三甲基硅基乙炔基)苄基甲醇收率 93%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

Under argon condition, 4-((trimethylsilyl)ethynyl)benzoic acid methyl ester (316 mg, 1.36 mmol) was dissolved in 5 mL of dry THF, and then cooled to 0° C., and LiAlH4 (2.04 mL, 1.0 M solution in THF, 2.04 mmol) was slowly added thereto. Upon completion of the reaction after stirring for 30 minutes at 0° C., the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and then 231 μL of water. When the white viscous precipitate was produced, the mixture was filtered through a silica pad to remove the precipitate. The resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 258 mg (1.26 mmol, 93%) of the desired compound.

后处理

  1. customUpon completion of the reaction
  2. customthe reaction was terminated
  3. additionby adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution
  4. customWhen the white viscous precipitate was produced
  5. filtrationthe mixture was filtered through a silica pad
  6. customto remove the precipitate
  7. concentrationThe resulting solution was concentrated by distillation under reduced pressure
  8. custompurified by column chromatography

来源与证据

ORD记录
ord-19996c85b8074865ab2da9e5ac55d734
来源数据集
uspto-grants-2014_08
专利号
US08809012B2

关联笔记

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