p-Toluenesulfonic acid → Methyl(2-heptafluoropropylbenzoxazol-5-yl)acetate

HRID 48163Notes

Reaction equation

HRID 48163 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](O)=[C:7]([NH:12][C:13](=[O:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[CH:6]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]2[O:24][C:13]([C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])=[N:12][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22742096Methyl (3-heptafluorobutyramido-4-hydroxyphenyl)acetate

Product 1

HCID 22742119Methyl(2-heptafluoropropylbenzoxazol-5-yl)acetateYield 67.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate (20.0 g, 0.053 mol) and para-toluenesulfonic acid (1.71 g) in toluene (150 ml) was heated at reflux (a Dean & Stark™ assembly was fitted to remove water) for 24 hours. The mixture was cooled to room temperature and the mixture was diluted with ethyl acetate (150 ml). The mixture was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane to give methyl(2-heptafluoropropylbenzoxazol-5-yl)acetate (12.9 g) as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux (a Dean & Stark™
  3. customassembly was fitted
  4. customto remove water) for 24 hours
  5. additionthe mixture was diluted with ethyl acetate (150 ml)
  6. washThe mixture was washed with saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-304f16db77184d9784d553da3fb1de77
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

Loading…