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

HRID 1088040Notes

Reaction equation

HRID 1088040 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-8d021a077e3248a9b8319f3cbe4dc192
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

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