反应详情

To an ice-cold solution of 4-(hydroxymethyl)imidazole hydrochloride (2.0 g, 15 mmol), N-hydroxyphthalimide (2.4 g, 15 mmol) and triphenylphosphine (4.0 g, 15 mmol) in THF (65 mL) was added a solution of diethyl azodicarboxylate (2.6 mL, 16 mmol) in THF (10 mL) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 18 h, the resultant precipitate was collected by vacuum filtration. The solid was partitioned between EtOAc (75 ml) and saturated NaHCO3 (75 mL). The aqueous layer was separated and extracted again with EtOAc (75 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, CH2Cl2 to 90:10 CH2Cl2/MeOH) gave 2-(1H-imidazol-4-ylmethoxy)-1,3-dihydro-2H-isoindole-1,3-dione (800 mg, 22%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ5.03 (2H, s), 7.30 (1H, s), 7.55 (1H, s), 7.81-7.86 (4H, m), 12.08 (1H, br s).

1. customThe stirred reaction mixture
2. filtrationthe resultant precipitate was collected by vacuum filtration
3. customThe solid was partitioned between EtOAc (75 ml) and saturated NaHCO3 (75 mL)
4. customThe aqueous layer was separated
5. extractionextracted again with EtOAc (75 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customPurification by column chromatography (silica gel, CH2Cl2 to 90:10 CH2Cl2/MeOH)