反应详情

To a solution of tert-butyl 4-vinylnaphthalen-1-ylcarbamate (31) (0.83 g, 3.08 mmol) in THF (10 mL) was added 9-BBN (0.5M in THF, 9.9 mL, 4.95 mmol) dropwise under nitrogen at 0° C. The mixture was warmed to RT and stirred for 16 hr. Water (1 mL), aqueous NaOH solution (3M, 10.0 mL, 30 mmol) and hydrogen peroxide (35% in water, 8.0 mL) were added. The reaction mixture was warmed to 50° C. and stirred for 2 hr and was then extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 10-60% ethyl acetate in isohexane, gradient elution) to afford the title compound (32) (0.763 g, 86%); m/z 288 (M+H)+, (ES+).

1. temperatureThe reaction mixture was warmed to 50° C.
2. stirringstirred for 2 hr
3. extractionwas then extracted with ethyl acetate
4. extractionThe ethyl acetate extract
5. washwas washed with water and brine
6. dry with materialdried (MgSO4)
7. customevaporated in vacuo
8. customThe residue was purified by flash column chromatography (SiO2, 10-60% ethyl acetate in isohexane, gradient elution)