反应详情

A mixture of, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (318 mg, 1 mmol), dimethylformamide (7.5 mL) and deionzed water (2.5 mL) was stirred at rt. Sodium cyanide (150 mg, 3.0 mmol) was added to reaction. After 3 h, dimethylformamide (10 mL) was added to help dissolve solids in reaction mixture. Let reaction mixture stir overnight at rt. Workup was done by washing reaction with brine (3×30 mL), extraction with EtOAc, combined organic extracts, dried (Na2SO4), filtered and removed solvent in vacuo. Flash chromatography of resulting orange solid on silica gel using a gradient elution of 1:9 EtOAc:hexanes to 1:3 EtOAc:hexanes afforded the desired intermediate, [4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile, as a light yellow solid.

1. dissolutionto help dissolve solids
2. customin reaction mixture
3. customreaction mixture
4. stirringstir overnight at rt
5. washby washing
6. customreaction
7. extractionwith brine (3×30 mL), extraction with EtOAc
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customremoved solvent in vacuo
11. customFlash chromatography of resulting orange solid on silica gel using
12. washa gradient elution of 1:9 EtOAc