N-Hydroxyphthalimide → Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

HRID 1732282Notes

Reaction equation

HRID 1732282 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CS(C)=O>[C:24]([O:23][C:21](=[O:22])[CH2:20][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetate

Product 1

HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetateYield 93.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 49 g of N-hydroxyphthalimide in 25 ml of dimethyl sulfoxide at 5° C., was added portionwise 27.6 g of potassium carbonate. After 10 minutes of stirring the reaction mixture was present as a red slurry to which 75 g of tert-butyl chloroacetate was added dropwise over 1 hour at 5° C. The resulting reaction mixture was stirred for 18 hours and poured into ice water. The solid product was filtered, dissolved in methylene chloride and washed with water. The methylene chloride phase was dried over magnesium sulfate, filtered and stripped and recrystallized from ethanol to give 77.5 g of 2-(2-tertbutoxy-2-oxoethoxy)-1H-isoindole-1,3(2H)-dione; m.p. 146°-7° C.

Workup

  1. additionwas added dropwise over 1 hour at 5° C
  2. customThe resulting reaction mixture
  3. stirringwas stirred for 18 hours
  4. filtrationThe solid product was filtered
  5. dissolutiondissolved in methylene chloride
  6. washwashed with water
  7. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9333dc7f02b84e77b322ce8a12387df2
Source dataset
uspto-grants-1980_12
Patent number
US04237123

Reaction notes

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