Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate → Ethyl 2-Phenoxy-4-Trifluoromethyl-5-Oxazolecarboxylate

HRID 1659286Notes

Reaction equation

HRID 1659286 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9](Cl)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Na]>CN(C=O)C.CCOCC>[O:22]([C:9]1[O:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:7]([C:12]([F:15])([F:14])[F:13])[N:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 12785855Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate2×HCID 66602278Sodium phenoxide

Product 1

HCID 12785857Ethyl 2-Phenoxy-4-Trifluoromethyl-5-Oxazolecarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The compound of Example 5, ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate (4.87 g; 0.02 mol) was added to a mixture of sodium phenol in 100 ml DMF. The reaction was allowed to progress at ambient temperature for 1 hour. Gas chromatographic analysis, at this point, indicated the completion of the reaction. The dark brown liquid was then slurried in ether and washed 5 times with NaOH (5%) and H2O. The resulting brown liquid was dried (MgSO4) and concentrated in vacuo to yield 5.2 g of a brown semi-solid. Bulb to bulb distillation at 75° C./25 mm gave 1.7 g of a colorless oil. Further distillation at 130° C./0.25 mm gave 2.8 g of a white solid. Recrystallization from methylcyclohexane gave 1.08 g of pure white solid, ethyl 2-phenoxy-4-trifluoromethyl-5-oxazolecarboxylate, mp 75°-77° C., yield 18%.

Workup

  1. customthe completion of the reaction
  2. washwashed 5 times with NaOH (5%) and H2O
  3. dry with materialThe resulting brown liquid was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49f85ae656f84e519675bc2b4e66042b
Source dataset
uspto-grants-1981_12
Patent number
US04303439

Reaction notes

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