Methyl vinyl ketone → 2-(3-Oxobutyl)isoindoline-1,3-dione

HRID 915678Notes

Reaction equation

HRID 915678 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH:12]([C:14]([CH3:16])=[O:15])=[CH2:13]>C(OCC)(=O)C.C(O)C.CC[O-].[Na+]>[O:15]=[C:14]([CH3:16])[CH2:12][CH2:13][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

6

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 6809Phthalimide

Product 1

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneYield 92.1%

Reagents, catalysts & solvents 3

HCID 2723922Sodium ethoxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepare a suspension of phthalimide (5 g, 34 mmol) in ethyl acetate (40 mL). Add methyl vinyl ketone (2.8 mL, 34 mmol) followed by NaOEt (116 mg, 1.7 mmol) in ethanol (10 mL). Stir the reaction at room temperature for 2 hours, then heat to reflux and stir for 3 hours. Concentrate the reaction in vacuo to a solid. Recrystallize the solid from ethanol to afford 2-(3-oxobutyl)isoindole-1,3-dione (6.8 g). 1H NMR (CDCl3) δ 7.82-7.88 (m, 2H), 7.69-7.77 (m, 2H), 3.97 (t, J=7 Hz, 2H), 2.88 (t, J=7 Hz, 2H), 2.20 (s, 3H).

Workup

  1. customPrepare
  2. customthe reaction at room temperature for 2 hours
  3. temperatureheat
  4. temperatureto reflux
  5. stirringstir for 3 hours
  6. concentrationConcentrate
  7. customthe reaction in vacuo to a solid
  8. customRecrystallize the solid from ethanol

Sources & evidence

ORD record
ord-f3f7e03491cd406c93b57d3713e6b709
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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