Salicylaldehyde → Benzofuran-2-yl-(5-methyl-3-phenyl-isoxazol-4-yl)-methanone

HRID 132599Notes

Reaction equation

HRID 132599 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4].[CH:17](=O)[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[CH:17]=[C:2]1[C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazole

Product 1

HCID 69106966Benzofuran-2-yl-(5-methyl-3-phenyl-isoxazol-4-yl)-methanoneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(bromoacetyl)-5-methyl-3-phenylisoxazole (commercially available) (140 mg, 0.5 mmol) in DMF (0.5 mL) was added salicylaldehyde (61 mg, 53 μL, 0.5 mmol) followed by potassium carbonate (138 mg, 1.0 mmol) and the resulting mixture stirred vigorously at room temperature for 2 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over Na2SO4 and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1) afforded the title compound (131 mg, 86%) as a white solid. MS m/e: 304.0 [M+H]+.

Workup

  1. additionThe mixture was then poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1)

Sources & evidence

ORD record
ord-4379a3071e2943828002ed1f4588bafc
Source dataset
uspto-grants-2008_06
Patent number
US07388025B2

Reaction notes

Loading…