Triethylamine → 3-(4-Benzyloxy-phenyl)-isoxazole-5-carbaldehyde

HRID 72325

反応式

HRID 72325 の反応式
[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

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 25517Ammonium ChlorideHCID 64164588[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-methanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 21912085Dimethylsulfoxide-dichloromethane溶媒

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-34655747a0874bf1ba2fad4898e979ab
出典データセット
uspto-grants-2014_09
特許番号
US08828992B2

関連ノート

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