2-Methoxyethanol → 2-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dione

HRID 656562Notes

Reaction equation

HRID 656562 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].O[N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][N:7]1[C:11](=[O:12])[C:10]2[C:9](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]1=[O:17]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 129191152-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dioneYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-methoxyethanol (2.00 g, 26.3 mmol), N-hydroxyphthalimide (4.72 g, 28.9 mmol, 1.1 eq., and triphenylphosphine (7.58 g, 28.9 mmol, 1.1 eq.) were dissolved in 85 mL of dry THF and then the mixture was cooled in an ice bath. Diisopropyl azodicarboxylate (6.91 g, 34.2 mmol, 1.3 eq.) was dissolved in 15 mL of dry THF and was added slowly to the above mixture. The reaction was stirred in the ice bath for 10 minutes and then the ice bath was removed. The reaction then was allowed to stir at room temperature under N2 overnight. The reaction was done by LC/MS and was concentrated to an oil. It was then purified by flash column chromatography using hexane/ethyl acetate 70/30 to give 2-(2-methoxyethoxy)isoindoline-1,3-dione (2A, 5.19 g, 89.2% yield). ESI-MS: m/z 222.3 (M+H)+.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. additionwas added slowly to the above mixture
  3. customthe ice bath was removed
  4. customThe reaction
  5. concentrationwas concentrated to an oil
  6. customIt was then purified by flash column chromatography

Sources & evidence

ORD record
ord-4bebbb1d223f44e6b89ea12aaee5cde0
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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