5-(3-Chlorophenyl)isoxazole-3-carbaldehyde → HCID 57528604, compound

HRID 1453800Notes

Reaction equation

HRID 1453800 reaction equation
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][N:14]=[C:13]([CH:16]=[O:17])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][N:14]=[C:13]([CH:16]([OH:17])[CH3:1])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 532992685-(3-Chlorophenyl)isoxazole-3-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 57528604HCID 57528604, compoundYield 124.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (3M in THF, 313 mL, 937.2 mmol) was added dropwise at 0° C. to 5-(3-chlorophenyl)isoxazole-3-carbaldehyde (177 g, 252 mmol) in THF (3 L). The mixture was allowed to attain room temperature, stirred at that temperature for 3 h and then quenched with aq. NH4Cl at 0° C. and the solvent was distilled off. To the remaining was added EtOAc and filtered through a plug of celite. The organic layer was washed with water, saturated brine and concentrated. The crude product was purified by flash column chromatography on silica using heptane/EtOAc=80:20, to give the title compound (70 g, 37%) as a white-yellow solid. 1H NMR: 7.73 (m, 1H), 7.63 (m, 1H), 7.38 (m, 2H), 6.57 (s, 1H), 5.07 (q, 1H), 2.44 (s, 1H), 1.59 (d, 3H).

Workup

  1. customto attain room temperature
  2. customquenched with aq. NH4Cl at 0° C.
  3. distillationthe solvent was distilled off
  4. additionTo the remaining was added EtOAc
  5. filtrationfiltered through a plug of celite
  6. washThe organic layer was washed with water, saturated brine
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-be1666f76bf8437ebc30b801d1080c5e
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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