Ethanol → HCID 20297518, compound

HRID 1389018Notes

Reaction equation

HRID 1389018 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([OH:16])=[O:15])[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>>[CH2:24]([O:15][C:14]([C:10]1[CH:11]=[N:12][O:13][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=1)=[O:16])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 20297516HCID 20297516, compound

Product 1

HCID 20297518HCID 20297518, compoundYield 80%

Procedure

A portion of the 5-(3'-trifluoromethylphenyl)-4-isoxazolecarboxylic acid (2.5 g.; 0.01 mol.) in 25 ml. of ethanol and 2 ml. of sulfuric acid were heated at reflux for 4 hours. The reaction mixture was cooled, concentrated to one-half its initial volume, then diluted with 175 ml. of methylene chloride. The organic solution was washed with water, sodium bicarbonate, again with water, dried over magnesium sulfate, filtered and concentrated to give an oil. The oil was distilled through a Vigreux column to yield ethyl-5-(3'-trifluoromethylphenyl)-4-isoxazolecarboxylate (2.2 g.; 80% yield) as a colorless oil (b.p.=88°-90° C. at 0.15 torr.) having the following analysis:

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated to one-half its initial volume
  4. additiondiluted with 175 ml
  5. washThe organic solution was washed with water, sodium bicarbonate, again with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil
  10. distillationThe oil was distilled through a Vigreux column

Sources & evidence

ORD record
ord-4666755adfbf46f3888dcb97e5769fb6
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

Loading…