三乙胺 → 3-(4-Benzyloxy-phenyl)-isoxazole-5-carbaldehyde

HRID 72325

反应方程式

HRID 72325 反应方程式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)=O.C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH:20]=[O:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

6

反应物 4

HCID 8471三乙胺HCID 24682三氧化硫HCID 25517氯化铵HCID 64164588[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-methanol

产物 1

HCID 118183053-(4-Benzyloxy-phenyl)-isoxazole-5-carbaldehyde

试剂、催化剂与溶剂 1

HCID 21912085Dimethylsulfoxide-dichloromethane溶剂

实验过程

[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol (1.0 g, 3.5 mmol) was dissolved in 60 ml of DMSO/methylene chloride (1:2), to which solution were added dropwise sulfur trioxide.pyridine complex (1.6 g, 10.5 mmol) and triethylamine (2.44 ml, 17.5 mmol), and stirred at 0° C. for about 2 hours. The completion of the reaction was confirmed by TLC, and 10 ml of NH4Cl was added to the solution. The residual solvent was distilled under reduced pressure, and then extracted three times with water and methylene chloride. An organic layer was washed with saline solution. The obtained organic layer was distilled under reduced pressure, followed by column chromatography (ethyl acetate/Hexane=1:2) to obtain 3-(4-benzyloxy-phenyl)-isoxazol-5-carbaldehyde as a desired solid compound.

后处理

  1. additionwas added to the solution
  2. distillationThe residual solvent was distilled under reduced pressure
  3. extractionextracted three times with water and methylene chloride
  4. washAn organic layer was washed with saline solution
  5. distillationThe obtained organic layer was distilled under reduced pressure

来源与证据

ORD记录
ord-34655747a0874bf1ba2fad4898e979ab
来源数据集
uspto-grants-2014_09
专利号
US08828992B2

关联笔记

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