2-Methoxypropene → 2-(1-Methoxy-1-methylethoxy)-1H-isoindole-1,3(2H)-dione

HRID 1662983Notes

Reaction equation

HRID 1662983 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH3:13][O:14][C:15]([CH3:17])=[CH2:16]>CC#N.C([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:13][O:14][C:15]([CH3:17])([O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7])[CH3:16]

Participants

6

Reactant 2

HCID 83002-MethoxypropeneHCID 10665N-Hydroxyphthalimide

Product 1

HCID 136082072-(1-Methoxy-1-methylethoxy)-1H-isoindole-1,3(2H)-dioneYield 75.5%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 20 g (123 mmol) of N-hydroxyphthalimide in 360 ml of CH3CN, 26.42 ml (276 mmol) of 2-methoxypropene and 42.36 mg (0.246 mmol) of anhydrous p-toluenesulfonic acid are added in portions at r.t. After stirring for 1 h, the mixture is diluted with 25 ml of sat. NaHCO3 and concentrated under reduced pressure. The residue is extracted with EtOAc and the organic layer is washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to give 21.84 g of 2-(1-methoxy-1-methyl-ethoxy)isoindole-1,3-dione as a white solid; NMR (CDCl3): 1.57 (s, 6H), 3.61 (s, 3H), 7.75 (dd, 2H, J=5.56 Hz, J=3.0 Hz), 7.83 (dd, 2H, J=5.56 Hz, J=3.0 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue is extracted with EtOAc
  3. washthe organic layer is washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b98cd7be8884c5ea0dc09af7c8184dd
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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