反应详情

温度

0 °C

To a suspension of methyltriphenylphosphonium bromide (3.82 g, 10.69 mmol) in THF (20 mL) at 0° C. under nitrogen was added potassium tert-butoxide (1.20 g, 10.69 mmol) and the reaction mixture was stirred at 0° C. for 15 min, then warmed to RT and stirred for a further 45 min. The suspension was cooled to 0° C. and a solution of tert-butyl 4-formylnaphthalen-1-ylcarbamate (30) (1.16 g, 4.28 mmol) in THF (10 mL) was added dropwise. The reaction mixture was warmed to RT and stirred for 2 hr. Saturated aqueous NH4Cl solution (30 mL) was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 0-10% ethyl acetate in isohexane, gradient elution) to afford the title compound (31) as a white solid (0.831 g, 72%): m/z 268 (m-H)− (ES−)

1. temperaturewarmed to RT
2. stirringstirred for a further 45 min
3. temperatureThe suspension was cooled to 0° C.
4. temperatureThe reaction mixture was warmed to RT
5. stirringstirred for 2 hr
6. extractionthe mixture was extracted with ethyl acetate
7. extractionThe ethyl acetate extract
8. washwas washed with brine
9. dry with materialdried (MgSO4)
10. customevaporated in vacuo
11. customThe residue was purified by flash column chromatography (SiO2, 0-10% ethyl acetate in isohexane, gradient elution)