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

HRID 72325

반응식

HRID 72325 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 21912085Dimethylsulfoxide-dichloromethane용매

실험 절차

[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.

후처리

  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

출처 및 근거

ORD 기록
ord-34655747a0874bf1ba2fad4898e979ab
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828992B2

연결된 노트

불러오는 중…