HCID 21829818, compound → 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanal

HRID 1600518Notes

Reaction equation

HRID 1600518 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]1=[O:14])C>O1CCCC1.O>[C:12]1(=[O:13])[N:8]([CH2:7][CH2:6][CH2:5][CH:4]=[O:3])[C:9](=[O:14])[CH:10]=[CH:11]1

Participants

4

Reactant 1

HCID 21829818HCID 21829818, compound

Product 1

HCID 218298204-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Maleimidobutyraldehyde diethylacetal (2 g, 8.29 mmol) in tetrahydrofuran (20 ml) and water (0.5 ml) was stirred under argon and DOWEX 50X8 ion exchange resin (H+, 2 g, ® Dow Chemical Co.) was added. After 12 hours stirring at room temperature, the solvent was decanted, dried (MgSO4) and evaporated in vacuo to afford 4-maleimidobutyraldehyde (formula III) as a yellow oil which rapidly solidified on standing (1.38 g, 99%); TLC Rf=0.4, ethyl acetate/hexane 1:1. The 4-maleimidobutyraldehyde turned out to be extremely unstable, so that it was necessary to do all work-up at low temperatures (0° C.) and under complete exclusion of oxygen (inert atmosphere).

Workup

  1. additionwas added
  2. customthe solvent was decanted
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-32d3267b0ba34968b2ce55dbe6da075e
Source dataset
uspto-grants-1999_11
Patent number
US05976783

Reaction notes

Loading…