5-Cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid methoxy-methyl-amide → 1-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone

HRID 2219406Notes

Reaction equation

HRID 2219406 reaction equation
CON(C)[C:4]([C:6]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:8][O:9][C:10]=1[CH:11]1[CH2:13][CH2:12]1)=[O:5].[CH3:21][Mg]Br>C1COCC1>[CH:11]1([C:10]2[O:9][N:8]=[C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:6]=2[C:4](=[O:5])[CH3:21])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 866135615-Cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, compound

Product 1

HCID 674211361-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanoneYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid methoxy-methyl-amide (4.00 g, 14.7 mmol) in THF (42 mL) cooled to −78° C. was added a solution of methylmagnesium bromide (3 M in diethylether, 9.80 mL, 29.4 mmol) dropwise within 5 min at −78° C. The cooling bath was removed and the reaction mixture was allowed to warm up to room temperature over 2.5 h. The reaction mixture was then re-cooled to −78° C., diluted with a saturated ammonium chloride solution (50 mL), allowed to warm up to room temperature and then diluted with water and extracted with ethyl acetate. The combined organic layers were then washed with brine and then dried over sodium sulphate and evaporated to afford the title compound (3.2 g, 94%) which was obtained as a light yellow solid. MS: m/e=228.3 [M+H]+.

Workup

  1. customThe cooling bath was removed
  2. temperatureThe reaction mixture was then re-cooled to −78° C.
  3. additiondiluted with a saturated ammonium chloride solution (50 mL)
  4. temperatureto warm up to room temperature
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layers were then washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-bc45c8c870b04db4935af2b7fe4facf6
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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