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ChemicalBook CAS DataBase List 2-(CYCLOPROPYLMETHOXY)-1H-ISOINDOLE-1,3(2H)-DIONE

2-(CYCLOPROPYLMETHOXY)-1H-ISOINDOLE-1,3(2H)-DIONE synthesis

2synthesis methods
-

Yield:113211-15-7 86%

Reaction Conditions:

with triphenylphosphine;diethylazodicarboxylate in tetrahydrofuran at 0; for 15 h;

Steps:

1G

Preparation of N-(cyclopropylmethoxy)phthalimide. To a suspension of cyclopropyl methanol (562 μl, 6.93 mmol), triphenylphosphine (2.02 g, 7.63 mmol) and N-hydroxyphthalimide (1.28 g, 7.63 mmol) in THF (10 mL) at 0° C. was added dropwise diethylazodicarboxylate (1.20 mL, 7.63 mmol) in THF (10 mL). The reaction mixture was allowed to stir for 15 h after which the solvent was removed under vacuum to dryness. Et2O (15 mL) was added to triturate the triphenylphosphine oxide and diethylhydrazinedicarboxylate, which was filtered off and washed with a little Et2O. The ethereal solution was concentrated under vacuum to give a residue which was filtered through a pad of silica (eluting with EtOAc/PE, 3:7). Removal of the solvent under reduced pressure afforded a pale yellow solid which was recrystallized from CH2Cl2/PE to give N-(cyclopropylmethoxy)phthalimide (1.30 g, 86%), as a white solid.

References:

US2006/63841,2006,A1 Location in patent:Page/Page column 26