N-Hydroxyphthalimide → 2-[2-(Ethenyloxy)ethoxy]-1H-isoindole-1,3(2H)-dione

Temperature

0 °C

Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2 H), 7.75 (m, 2 H), 6.46 (dd, J=14.3, 6.7 Hz, 1 H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3 H).

1. customthe resultant reaction mixture
2. temperatureto warm to ambient temperature over 18 h
3. concentrationThe reaction mixture was concentrated to a paste
4. filtrationthe solids were filtered
5. washwashed with chloroform
6. concentrationThe filtrate was further concentrated
7. filtrationfiltered again
8. washwashing the solids with chloroform
9. concentrationThe remaining chloroform solution was concentrated to an oil
10. dissolutionThe oil was dissolved in absolute ethanol (75 mL)
11. customcrystallization
12. customThe crystals were collected
13. customrecrystallized from hot ethanol

ORD record

ord-7b4e648515c74e31beefb8132ab9a184

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07411001B2