反应详情

A mixture of 5-hydroxyphthalide (1.0 g, 6.66 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (1.49 g, 8.01 mmol), potassium carbonate (2.3 g, 16.6 mmol) and sodium iodide (1.0 g, 6.67 mmol) in ethanol (40 ml) was stirred at reflux under nitrogen for 18 hours. The mixture was cooled to room temperature, and filtered through celite. The filtrate solution was evaporated to dryness. The residue was partitioned between EtOAc (75 ml) and 2M HCl solution (50 ml). The organic layer was extracted with 2M HCl (2×30 ml). The aqueous layers were combined, basified with NaOH aqueous solution, and extracted with CHCl3 (3×50 ml). The organic layers were combined, dried over anhydrous Na2SO4, and evaporated to a light brown solid, which was triturated with CHCl3/Hexanes to give 5-(2-morpholin-4-yl-ethoxy)-3H-isobenzofuran-1-one as white crystals (1.43 g, 82%).

1. temperatureat reflux under nitrogen for 18 hours
2. filtrationfiltered through celite
3. customThe filtrate solution was evaporated to dryness
4. customThe residue was partitioned between EtOAc (75 ml) and 2M HCl solution (50 ml)
5. extractionThe organic layer was extracted with 2M HCl (2×30 ml)
6. extractionextracted with CHCl3 (3×50 ml)
7. dry with materialdried over anhydrous Na2SO4
8. customevaporated to a light brown solid, which
9. customwas triturated with CHCl3/Hexanes