N-Hydroxyphthalimide → 2-[(Cyclohex-2-en-1-yl)oxy]-1H-isoindole-1,3(2H)-dione

HRID 371237Notes

Reaction equation

HRID 371237 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.O[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:2]1([O:1][N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 131982-Cyclohexen-1-OL

Product 1

HCID 135771062-[(Cyclohex-2-en-1-yl)oxy]-1H-isoindole-1,3(2H)-dioneYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-hydroxycyclohexene (4.0 g), N-hydroxyphthalimide (6.7 g) and triphenyl phosphine (9.2 g) in tetrahydrofuran (200 ml) was stirred at room temperature. After the addition of diethyl azoformate (7.9 g), the resulting mixture was stirred for 20 hours at room temperature. The reaction mixture was evaporated and the residue was subjected to column chromatography on silica gel (80 g), using chloroform as an eluent. The fractions containing the objected compounds were combined and evaporated to give N-(2-cyclohexen-1-yl)oxyphthalimide (6.5 g).

Workup

  1. stirringthe resulting mixture was stirred for 20 hours at room temperature
  2. customThe reaction mixture was evaporated
  3. additionThe fractions containing the objected compounds
  4. customevaporated

Sources & evidence

ORD record
ord-df717b1acbdb4e8a8f9e2f7cf469ac7f
Source dataset
uspto-grants-1985_07
Patent number
US04529802

Reaction notes

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