Phthalimide potassium salt → 2-(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-isoindole-1,3-dione

HRID 1807542Notes

Reaction equation

HRID 1807542 reaction equation
[K].[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12.[CH2:13]([C:17]1[C:21]([CH2:22]Cl)=[C:20]([CH3:24])[O:19][N:18]=1)[CH2:14][CH2:15][CH3:16]>CN(C=O)C.O>[CH2:13]([C:17]1[C:21]([CH2:22][N:6]2[C:2](=[O:12])[C:3]3[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:5]2=[O:7])=[C:20]([CH3:24])[O:19][N:18]=1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 66643618HCID 66643618, compound

Product 1

HCID 666459502-(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-isoindole-1,3-dioneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

Phthalimide potassium was suspended in DMF (35 mL) and the reaction mixture heated to 90° C. A solution of 3-butyl-4-chloromethyl-5-methyl-isoxazole (970 mg, 5.2 mmol) in DMF (25 mL) was added. After 45 min the reaction mixture was cooled, evaporated and the residue obtained was diluted with water then extracted with ether. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (1.21 g, 78%) as an off white solid that was used directly in the next step.

Workup

  1. temperatureAfter 45 min the reaction mixture was cooled
  2. customevaporated
  3. customthe residue obtained
  4. extractionthen extracted with ether
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthen purified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5d948be69eb44049a88f49fbf197a9c4
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

Loading…