反应详情

A solution of N-acetylethanolamine (10.0 g, 6.79 ml, 97 mmol) in a mixture of anhydrous tetrahydrofuran (100 ml) and dimethylformamide (10 ml) was added to a stirred suspension of 80% sodium hydride in oil dispersion (2.90 g, 97 mmol) in dry tetrahydrofuran (140 ml), under nitrogen, at room temperature. After 1 hour, the reaction mixture was heated to 40°-50° C. and then, after a further 0.5 hour, cooled to ice-bath temperature. Next, benzyl bromide (13.8 ml, 116 mmol) was added and the resulting suspension stirred at room temperature for 18 hours, before being cautiously quenched with water (400 ml). The resulting mixture was extracted with ethyl acetate (2×300 ml) and the combined extracts washed with water (200 ml), dried (Na2SO4) and evaporated under reduced pressure. The resulting residue was partitioned between ethyl acetate and water, then the organic phase washed thrice with water, dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with a solvent gradient of methanol:ethyl acetate (0:100 to 10:90), to give the required product (7.8 g) as an oil. Rf 0.21 (SS 17). LRMS: m/z 194.3 (M+1)+.

1. temperaturethe reaction mixture was heated to 40°-50° C.
2. waitafter a further 0.5 hour
3. temperaturecooled to ice-bath temperature
4. custombefore being cautiously quenched with water (400 ml)
5. extractionThe resulting mixture was extracted with ethyl acetate (2×300 ml)
6. washthe combined extracts washed with water (200 ml)
7. dry with materialdried (Na2SO4)
8. customevaporated under reduced pressure
9. customThe resulting residue was partitioned between ethyl acetate and water
10. washthe organic phase washed thrice with water
11. dry with materialdried (Na2SO4)
12. customevaporated under reduced pressure
13. customThe crude product was purified by column chromatography on silica gel
14. washeluting with a solvent gradient of methanol:ethyl acetate (0:100 to 10:90)