Water → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

HRID 600943Notes

Reaction equation

HRID 600943 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1.O>CS(C)=O>[CH:19]1([O:7][N:8]2[C:9](=[O:18])[C:10]3[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:13])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 10665N-HydroxyphthalimideHCID 11430Potassium Carbonate

Product 1

HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

Solid potassium carbonate (8.64 g, 62.5 mmol) was added to a solution of N-hydroxyphthalimide (4.08 g, 25.0 mmol) in dimethyl sulfoxide (38 mL), and the mixture was stirred at 25° C. for 5 min. To the mixture cyclopentyl bromide (37.5 mmol, 4.02 mL) was added, and the mixture stirred at 80° C. for 3 h. After cooling in ice, the mixture was poured into cold water and the resulting precipitate was collected by filtration in vacuo, washed with water (25 mL) and hexanes (15 mL) and dried in vacuo to afford 2-cyclopentyloxy-isoindole-1,3-dione (4.89 g, 85%) as an off-white solid which was used in the next step without further purification.

Workup

  1. stirringthe mixture stirred at 80° C. for 3 h
  2. temperatureAfter cooling in ice
  3. filtrationthe resulting precipitate was collected by filtration in vacuo
  4. washwashed with water (25 mL) and hexanes (15 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cbc878c9bfd541b88f39d2f4318675a8
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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