Hydrochloric Acid → HCID 69292316, compound

HRID 747582Notes

Reaction equation

HRID 747582 reaction equation
C[Mg]I.[CH2:4](N(CC)CC)C.C(O[C:14]([C:16]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[O:18][N:17]=1)=[O:15])C.Cl>C1(C)C=CC=CC=1>[F:30][C:27]([F:28])([F:29])[C:23]1[CH:22]=[C:21]([C:19]2[O:18][N:17]=[C:16]([C:14](=[O:15])[CH3:4])[CH:20]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 53439058Ethyl 5-[3-(trifluoromethyl)phenyl]-1,2-oxazole-3-carboxylateHCID 178418373HCID 178418373, compound

Product 1

HCID 69292316HCID 69292316, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a cooled (5-10° C.) solution of 4.6 ml (0.014 mol) methyl magnesium iodide solution (3M in diethyl ether) and 5.8 ml (0.042 mol) triethylamine in 10 ml toluene, a solution of 2.06 g (0.00723 mol) 5-(3-trifluoromethyl-phenyl)-isoxazole-3-carboxylic acid ethyl ester in 20 ml toluene was added dropwise. After the addition was complete, the reaction mixture was stirred at 0-5° C. for 2 h and then treated with 5.6 ml 4N aqueous HCl solution. The mixture was filtered over celite. The aqueous phase was separated and the organic layer was washed with water, 5% aqueous NaHCO3 solution and twice with water. The organic phase was dried over magnesium sulfate and the solvent was evaporated. The residue was dissolved in a mixture of 28 ml MeOH and 0.45 ml 20% aqueous KOH solution. The solution was heated to 45° C. for 30 min, then cooled and acidified to pH 2 by addition of 6N HCl. The solvent was evaporated and the residue was mixed with toluene and aqueous NaHCO3 solution. The mixture was filtered over celite. The organic layer was separated and the solvent was evaporated to yield 0.7 g (0.00274 mol) 1-[5-(3-trifluoromethyl-phenyl)-isoxazol-3-yl]-ethanone.

Workup

  1. additionAfter the addition
  2. filtrationThe mixture was filtered over celite
  3. customThe aqueous phase was separated
  4. washthe organic layer was washed with water, 5% aqueous NaHCO3 solution and twice with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in a mixture of 28 ml MeOH and 0.45 ml 20% aqueous KOH solution
  8. temperatureThe solution was heated to 45° C. for 30 min
  9. temperaturecooled
  10. additionacidified to pH 2 by addition of 6N HCl
  11. customThe solvent was evaporated
  12. additionthe residue was mixed with toluene and aqueous NaHCO3 solution
  13. filtrationThe mixture was filtered over celite
  14. customThe organic layer was separated
  15. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b8212ef6a5874c4e8a61d9b1e69f3f16
Source dataset
uspto-grants-2008_07
Patent number
US07396944B2

Reaction notes

Loading…