Реакция #624553

Уравнение реакции

HCl

4-methoxypyridine

THF

Cbz-Cl

→

benzyl 2-allyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

Растворители

ether

Условия реакции

Обработка

1. 1
   Другоеto form a yellow suspension
2. 2
   ЭкстракцияThe reaction mixture was extracted with ethyl acetate
3. 3
   ДругоеAfter removal of solvent
4. 4
   Другоеthe crude product was purified by silica gel chromatography (gradient, 10% to 25% EtOAc/hexanes)

Методика

At −23° C., to a solution of 4-methoxypyridine (5.45 g, 50 mmol) in THF (50 mL), 1.0 N Allyl-MgBr (50 mL, 50 mmol) in ether was added to form a yellow suspension. 95% Cbz-Cl (7.4 mL, 50 mmol) was then added dropwise. The yellow mixture was stirred at −23° C. for 30 mins and then poured into 10% HCl (100 mL). The reaction mixture was extracted with ethyl acetate. After removal of solvent, the crude product was purified by silica gel chromatography (gradient, 10% to 25% EtOAc/hexanes) to give benzyl 2-allyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate 129. LC/MS RT (2.25 min method)=1.090 min. Mass observed: 272.1 (M+H).

Источник