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

HRID 72325

Reaktionsgleichung

Reaktionsgleichung von HRID 72325
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21912085Dimethylsulfoxide-dichloromethaneLösungsmittel

Versuchsvorschrift

[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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-34655747a0874bf1ba2fad4898e979ab
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828992B2

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