反应 #8730

反应方程式

2-fluoro-4-nitrobenzotrifluoride

(R)-1-methyl-pyrrolidin-3-ol

sodium hydride

→

oil

收率 46.0%

2-((R)-1-Methyl-pyrrolidin-3-yloxy)-4-nitrobenzotrifluoride

收率 46.0%

溶剂

MeOH EtOAc

tetrahydrofuran

反应条件

后处理

1. 1
   其他Without removing the ice bath
2. 2
   其他to come to room temperature
3. 3
   其他Quenched with water (50 ml) and brine (100 ml)
4. 4
   萃取then extracted into diethyl ether (5×100 ml)
5. 5
   干燥Extracts dried over anhydrous magnesium sulfate
6. 6
   其他for 1 hr
7. 7
   过滤Filtered through Celite
8. 8
   workup.ADDITIONThe filtrate was treated with silica (35 g)
9. 9
   其他then evaporated
10. 10
    其他to give the crude product

实验过程

A solution of 2-fluoro-4-nitrobenzotrifluoride (12.4 g, 59.3 mmol, 1.0 eq) and (R)-1-methyl-pyrrolidin-3-ol (6.0 g, 59.3 mmol, 1.0 eq) in anhydrous tetrahydrofuran (150 ml) was cooled to 0° C. then slowly treated with portions of 60% sodium hydride (4.7 g, 0.12 mol, 2 eq) over 5 min. Without removing the ice bath, the reaction was allowed to come to room temperature and stir for 48 hrs. Quenched with water (50 ml) and brine (100 ml) then extracted into diethyl ether (5×100 ml). Extracts dried over anhydrous magnesium sulfate and decolorizing charcoal for 1 hr. Filtered through Celite. The filtrate was treated with silica (35 g) then evaporated to give the crude product suspended on silica. Column chromatography on silica (1% MeOH/EtOAc→5% MeOH/EtOAc) gave the product (Rf≡0.3 in 1% MeOH/EtOAc) as an orange oil (7.85 g, 46%).

来源