Triethylamine → HCID 19976954, compound

HRID 1742528Notes

Reaction equation

HRID 1742528 reaction equation
Cl[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=O.[CH:9]#[C:10][CH:11](O)CC.C(N([CH2:20][CH3:21])CC)C.CC(C)=[O:24].OS(O)(=O)=O.O=[Cr](=O)=O>C(Cl)(Cl)Cl.CC(C)=O.N1C=CC=CC=1>[CH2:9]([C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH2:20][CH3:21])[O:24][N:2]=1)[CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 929811-Pentyn-3-olHCID 131709961Jones' reagent

Product 1

HCID 19976954HCID 19976954, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Dissolved in 50 ml of chloroform were 5.0 g (57.5 mmol) of n-butylaldoxime and 0.3 ml of pyridine, to which 7.6 g (57.1 mmol) of N-chlorosuccinimide were added in small portions while the internal temperature was controlled not to exceed 35° C. After the addition, the resultant mixture was stirred at room temperature for 1 hour. To the solution, 6.0 g (71.4 mmol) of 1-pentyn-3-ol and 5.9 g (58.4 mmol) of triethylamine were added. The stirring was continued for 2 hours at 40°-50° C. After the solvent was distilled off under reduced pressure, water was added and the reaction product was then extracted with diethyl ether. After concentration, the residue was purified by silica gel chromatography (eluent: chloroform) so that 3-propyl-5-(1-hydroxypropyl)isoxazole was obtained. It was dissolved in acetone, oxidized with Jones' reagent under ice cooling, and purified by silica gel chromatography (eluent: chloroform) , so that 3 -propyl-5-propionylisoxazole was obtained as colorless oil. Analytical results of the oil obtained: Yield: 6.9 g (72%).

Workup

  1. customto exceed 35° C
  2. additionAfter the addition
  3. distillationAfter the solvent was distilled off under reduced pressure, water
  4. additionwas added
  5. extractionthe reaction product was then extracted with diethyl ether
  6. concentrationAfter concentration
  7. customthe residue was purified by silica gel chromatography (eluent: chloroform) so that 3-propyl-5-(1-hydroxypropyl)isoxazole
  8. customwas obtained
  9. custompurified by silica gel chromatography (eluent: chloroform) , so that 3 -propyl-5-propionylisoxazole
  10. customwas obtained as colorless oil
  11. customAnalytical results of the oil
  12. customobtained

Sources & evidence

ORD record
ord-51b1c77b1ec34439b2bc010e11a2806b
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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