HCID 58082769, compound → HCID 57497166, compound

HRID 1626119Notes

Reaction equation

HRID 1626119 reaction equation
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[N:10]=[C:11]([CH3:18])[O:12][C:13]=1[C:14]([F:17])([F:16])[F:15])=[O:8]>C(OCC)C>[CH3:18][C:11]1[O:12][C:13]([C:14]([F:15])([F:16])[F:17])=[C:9]([C:7](=[O:8])[CH3:1])[N:10]=1

Participants

4

Reactant 2

HCID 58082769HCID 58082769, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57497166HCID 57497166, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under an atmosphere of nitrogen, a solution of methylmagnesium bromide (3M in diethylether; 0.63 ml, 1.89 mmol) was cooled to 0° C. A solution of 2-methyl-5-trifluoromethyl-oxazole-4-carboxylic acid methoxy-methyl-amide (300 mg, 1.26 mmol) in diethylether (3 ml) was added dropwise. The reaction mixture was left to warm to room temperature and stirring was continued for 15 minutes. For the workup, the reaction mixture was cooled to 0° C. and quenched with hydrochloric acid (1N, 3 ml). After 5 minutes of stirring, the mixture was extracted with diethylether. The organic layer was dried over sodium sulphate, then evaporated. The crude product was purified by chromatography on silica gel using a 4:1-mixture of cyclohexane and ethyl acetate as the eluent. The 1-(2-methyl-5-trifluoromethyl-oxazol-4-yl)-ethanone (155 mg, 64% yield) was obtained as a colorless liquid.

Workup

  1. waitThe reaction mixture was left
  2. temperatureFor the workup, the reaction mixture was cooled to 0° C.
  3. customquenched with hydrochloric acid (1N, 3 ml)
  4. stirringAfter 5 minutes of stirring
  5. extractionthe mixture was extracted with diethylether
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customevaporated
  8. customThe crude product was purified by chromatography on silica gel using a 4

Sources & evidence

ORD record
ord-eb65175da50441babe7b7dc8629b63da
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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