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

HRID 72325

Reaction equation

HRID 72325 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

[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.

Workup

  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

Sources & evidence

ORD record
ord-34655747a0874bf1ba2fad4898e979ab
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Linked notes

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