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

HRID 328449Notes

Reaction equation

HRID 328449 reaction equation
Cl[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[OH:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].C(N(CC)CC)C.CN(C)C=O>O>[C:6]([O:5][C:3]([CH2:2][O:10][N:11]1[C:12](=[O:21])[C:13]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]2[C:15]1=[O:16])=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 66052tert-Butyl chloroacetate

Product 1

HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetateYield 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

t-Butyl chloroacetate (13.0g, prepared according to Org. Synth., Coll.Vol. 4, 263) was added dropwise to a stirred mixture of N-hydroxyphthalimide (14.2g), triethylamine (23.0g), and dimethylformamide (30ml), and the resulting mixture was stirred for 4 hr. The mixture was poured into water (500 ml), and the precipitated solid was collected, washed with water, and dried. Recrystallisation from ethanol gave N-t-butoxycarbonylmethoxyphthalimide (17.26g, 72%); m.p. 145.6°; τ values (DMSO-d6) 2.09 (4 Ar-H), 5.28 (CH2), 8.56 (But).

Workup

  1. customthe precipitated solid was collected
  2. washwashed with water
  3. customdried
  4. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-b72f1224aa9840f38658df72fb29a642
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Reaction notes

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