反应详情

To a solution of primary alcohol (21, 1.5 g, 2.04 mmol) from Step 1 in N,N-dimethylformamide (10 mL) at 0° C. under an atmosphere of nitrogen was added sodium hydride (60% dispersion in mineral oil, 123 mg, 3.06 mmol), and the mixture was stirred for 30 min at the same temperature. Then allyl bromide (0.26 mL, 3.06 mmol) was added dropwise, and the mixture was stirred with gradual warming to ambient temperature over 5 h. After re-cooling to 0° C., the reaction mixture was quenched by addition of water (10 mL). The mixture was diluted with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 20% tetrahydrofuran in hexanes gradient) to yield the title compound (22, 1.12 g, 1.44 mmol, 71%) as a white solid.

1. stirringthe mixture was stirred
2. temperatureAfter re-cooling to 0° C.
3. customthe reaction mixture was quenched by addition of water (10 mL)
4. additionThe mixture was diluted with saturated ammonium chloride
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customevaporated in vacuo
10. customThe resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 20% tetrahydrofuran in hexanes gradient)