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

HRID 1754838Notes

Reaction equation

HRID 1754838 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.[CH3:12][C:13](=[O:16])[CH:14]=[CH2:15].[O-]CC.[Na+]>C(OCC)(=O)C.C(O)C>[O:16]=[C:13]([CH3:12])[CH2:14][CH2:15][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 3

HCID 6570Methyl vinyl ketoneHCID 6809PhthalimideHCID 2723922Sodium ethoxide

Product 1

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a well-stirred milky suspension of phthalimide (60.0 g, 408.0 mmol, 1.00 eq.) and 3-buten-2-one (33.2 mL, 408.0 mmol, 1.00 eq.) in anhydrous ethyl acetate (400 mL) under N2, a freshly prepared yellow homogeneous solution of sodium ethoxide (1.4 g, 20.4 mmol, 0.05 eq.) in anhydrous ethanol (100 mL) was added dropwise (over 35 min.). After completion of the addition, the resulting slightly yellow heterogeneous mixture was further stirred at r.t. for 2 hours. The beige heterogeneous mixture was then refluxed (oil bath temperature=90° C.) for 2 hours. The resulting orange homogeneous solution was then allowed to slowly cool down to r.t. The resulting heterogeneous mixture was concentrated to dryness in vacuo to afford a beige solid which was recrystallized from EtOH to afford the title compound as a beige solid.

Workup

  1. additionAfter completion of the addition
  2. temperatureThe beige heterogeneous mixture was then refluxed (oil bath temperature=90° C.) for 2 hours
  3. temperatureto slowly cool down to r.t
  4. concentrationThe resulting heterogeneous mixture was concentrated to dryness in vacuo
  5. customto afford a beige solid which
  6. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-e73f0a9cf57e4d67a500bcb6c6254dfb
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

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