Dimethylformamide → 2-[(Oxolan-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1734142Notes

Reaction equation

HRID 1734142 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH:6]1[CH2:10][CH2:9][O:8][CH2:7]1)(=O)=O.[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].CN(C=O)C>O>[O:8]1[CH2:9][CH2:10][CH:6]([CH2:5][N:22]2[C:18](=[O:28])[C:19]3=[CH:27][CH:26]=[CH:25][CH:24]=[C:20]3[C:21]2=[O:23])[CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 15335290Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl esterHCID 24194345Phthalimide potassium salt

Product 1

HCID 223990302-[(Oxolan-3-yl)methyl]-1H-isoindole-1,3(2H)-dioneYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture comprising 30.0 g of (tetrahydro-3-furanyl)methyl tosylate, 23.0 g of potassium phthalimide and 150 ml of DMF was stirred at 80° C. for 8 hours. Water was poured into the reaction mixture, and crystals precipitated out was separated by filtration to obtain 27.0 g of N-{(tetrahydro-3-furanyl)methyl}phthalimide.

Workup

  1. customprecipitated out
  2. customwas separated by filtration

Sources & evidence

ORD record
ord-91ad557b73c7456cbbade5a328233040
Source dataset
uspto-grants-1996_07
Patent number
US05532365

Reaction notes

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