反応 #1123665

反応方程式

1,2-Dimethoxyethane

(R)-4-[5-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one

4-trifluoromethoxy phenylboronic acid

sodium carbonate

→

title compound

収率 83.4%

(R)-4-(6-(trans-4-tert-butylcyclohexyloxy)-5-(4-(trifluoromethoxy)phenyl)naphthalen-2-yl)-4-methyloxazolidin-2-one

収率 83.4%

溶媒

Water

water

Ethylacetate

反応条件

後処理

1. 1
   その他vial equipped with a magnetic stir bar
2. 2
   その他The vial was degassed
3. 3
   その他purged with nitrogen
4. 4
   workup.WAITAfter 3 h
5. 5
   その他the layers were separated
6. 6
   乾燥The combined organic phase was then dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他purified by flash chromatography (0-55% EtOAc in hexane)

実験手順

(R)-4-[5-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.2079 g, 0.0004516 mol), 4-trifluoromethoxy phenylboronic acid (0.130 g, 0.000632 mol), tetrakis(triphenylphosphine)palladium(O) (0.03 g, 0.00002 mol) and sodium carbonate (0.191 g, 0.00181 mol) were added to a capped 40 mL EPA vial equipped with a magnetic stir bar. The vial was degassed and purged with nitrogen. 1,2-Dimethoxyethane (5.00 mL, 0.0481 mol) was added and the mixture was stirred for 5 minutes. Water (3.00 mL, 0.166 mol) was then added and the mixture was heated at 95° C. After 3 h, HPLC analysis showed that the reaction was complete. Ethylacetate (5 mL) and water (5 mL) were added and the layers were separated. The combined organic phase was then dried over MgSO4, filtered, concentrated and purified by flash chromatography (0-55% EtOAc in hexane) to give 204.1 mg of the title compound (83% yield).

出典