Reaction #1106684

ord-4fe71c02721f4ff59e9c4d6ff489777e

Reaction equation

O=C1NC(=O)c2ccccc21.[K]
potassium phthalimide
O
water
CN(C)C=O
DMF
O=C1c2ccccc2C(=O)N1C[C@H]1COc2ccccc2O1
(2S)-2-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-isoindole-1,3-dione

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureheated
  2. 2
    Temperatureto reflux for 1 h
  3. 3
    FiltrationWhite solid was filtered
  4. 4
    Washthe solid was washed several times with water, 2% NaOH, and water again
  5. 5
    Otherdry

Procedure

The white solid was combined with potassium phthalimide (14.4 g, 78 mmol) in DMF (250 mL) and heated to reflux for 1 h, cooled to room temperature and poured into vigorously stirring water (1.5 L) and stirred 30 min. White solid was filtered and the solid was washed several times with water, 2% NaOH, and water again and let air dry to yield a (2S)-2-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-isoindole-1,3-dione as white powdery solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08716231B2uspto-grants-2014_05