N-Hydroxyphthalimide → 2-(3-Methoxy-4-pent-2-ynyloxy-benzyloxy)-isoindole-1,3-dione

HRID 458246Notes

Reaction equation

HRID 458246 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14])=[C:5]([O:15][CH3:16])[CH:4]=1.[OH:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].[OH-].[K+]>CN(C)C=O.CO>[CH3:16][O:15][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14])[CH2:2][O:17][N:18]1[C:22](=[O:23])[C:21]2[C:20](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]1=[O:28]

Participants

6

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 14797Potassium HydroxideHCID 184420934-Chloromethyl-2-methoxy-1-pent-2-ynyloxy-benzene

Product 1

HCID 184420912-(3-Methoxy-4-pent-2-ynyloxy-benzyloxy)-isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-Chloromethyl-2-methoxy-1-pent-2-ynyloxy-benzene (28 g, 0.12 mol) and N-hydroxyphthalimide (19.5 g, 0.12 mol) are dissolved in 180 ml of N,N-dimethylformamide. The reaction mixture is heated to +70° C. and potassium hydroxide (24 ml of a 5 M solution in methanol, 0.12 mol) is added at this temperature. The reaction is stirred for 1 hour at +70° C., subsequently cooled to room temperature and poured on water. This mixture is stirred for one further hour and filtered. The resulting crystalls are washed with water and recrystallized from methanol/acetone (8:1) to yield 2-(3-methoxy-4-pent-2-ynyloxy-benzyloxy)-isoindole-1,3-dione as colourless crystalls.

Workup

  1. temperatureThe reaction mixture is heated to +70° C.
  2. additionpoured on water
  3. stirringThis mixture is stirred for one further hour
  4. filtrationfiltered
  5. washThe resulting crystalls are washed with water
  6. customrecrystallized from methanol/acetone (8:1)

Sources & evidence

ORD record
ord-4357ef393f964306862bd9846e1d81b5
Source dataset
uspto-grants-2007_03
Patent number
US07189873B2

Reaction notes

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