반응 #8730

반응 방정식

2-fluoro-4-nitrobenzotrifluoride

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

sodium hydride

→

oil

수율 46.0%

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

수율 46.0%

용매

MeOH EtOAc

tetrahydrofuran

반응 조건

후처리

1. 1
   기타Without removing the ice bath
2. 2
   기타to come to room temperature
3. 3
   기타Quenched with water (50 ml) and brine (100 ml)
4. 4
   추출then extracted into diethyl ether (5×100 ml)
5. 5
   건조Extracts dried over anhydrous magnesium sulfate
6. 6
   기타for 1 hr
7. 7
   여과Filtered through Celite
8. 8
   workup.ADDITIONThe filtrate was treated with silica (35 g)
9. 9
   기타then evaporated
10. 10
    기타to give the crude product

실험 절차

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%).

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