N-Hydroxyphthalimide → 2-(Cyclopent-3-enyloxy)isoindoline-1,3-dione

HRID 1614067Notes

Reaction equation

HRID 1614067 reaction equation
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.O[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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([O:6][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2814783-Cyclopenten-1-ol

Product 1

HCID 197740932-(Cyclopent-3-enyloxy)isoindoline-1,3-dioneYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 3-cyclopenten-1-ol (15.3 g), N-hydroxyphthalimide (29.7 g) and triphenylphosphine (47.7 g) in tetrahydrofuran (250 ml) was added diethyl azodicarboxylate (31.7 g) at 40° to 50° C. After stirring at 45° C. for 2 hours, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The separated organic layer was washed with 5% aqueous solution of sodium bicarbonate, brine, successively and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residual oil was subjected to column chromatography on silica gel. The desired product was eluted with 15% ethyl acetate in n-hexane to give N-(3-cyclopenten-1-yloxy)phthalimide (25.6 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with 5% aqueous solution of sodium bicarbonate, brine
  3. dry with materialsuccessively and dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. washThe desired product was eluted with 15% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-149b2c5b5ccb41d99ccc5a2f9791eeaa
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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