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

HRID 131061Notes

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+].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20]>CN1CCCC1=O>[C:3]1(=[O:12])[N:2]([O:1][CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]12

Participants

Conditions

Temperature: 50 °C

Procedure

N-hydroxyphthalimide (3.87 g, 23 mmol) and potassium carbonate (2.14 g, 15.5 mmol) were suspended in 1-methyl-2-pyrrolidinone (23 mL) and heated to 40° C. t-Butyl-bromoacetate (4.58 g, 23 mmol) was added, and the reaction temperature was increased to 50° C., and held at this temperature for 4 hours, and then poured into 50 mL of ice water to precipitate the product. The solid was collected on a glass filter funnel and washed with water until the filtrate was colorless. The precipitate was dried on the filter funnel with the house vacuum, and by azeotroping with chloroform. This afforded 5.92 g (91% yield) of product with a melting point of 143-144° C. The compound was characterized as NMR and MS as follows: 1) C-NMR (CDCl3): 28.39, 73.82, 83.38, 124.04, 129.22, 134.99, 163.40, 166.29 ppm; 2) H-NMR (CDCl3): 1.46 (s, 9H); 4.68 (s, 2H); 7.74 (m, 2H); 7.83 (m, 2H) ppm; and 3) MS (ESI): 300.2 [M+Na]+, 577.3 [2M+Na]+.

Workup

additionwas added
customto precipitate the product
customThe solid was collected on a glass
filtrationfilter funnel
washwashed with water until the filtrate
customThe precipitate was dried on the filter funnel with the house vacuum
customby azeotroping with chloroform

Sources & evidence

ORD record: ord-44af863cc5ce4ec5a5d1c630d052e2dd
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384558B2

Reaction notes

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