Reaktion #1248556

Reaktionsgleichung

4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine

2-fluoro-5-methoxy-3-triisopropylsilanyloxybenzaldehyde

trimethylsilyl cyanide

Yb(OTf)3

→

title compound

(2-fluoro-5-methoxy-3-triisopropylsilanyloxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Lösungsmittel

Ethyl acetate

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashing
2. 2
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
3. 3
   FiltrationThe desiccating agent was filtered off
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Vorschrift

After adding 5.47 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 10.2 g of 2-fluoro-5-methoxy-3-triisopropylsilanyloxybenzaldehyde, 10 g of MS3A and 6.2 ml of trimethylsilyl cyanide to a solution of 1.94 g of Yb(OTf)3 in 100 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred for 3 days at room temperature. Ethyl acetate was added to the reaction mixture, and washing was performed with water. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (9.01 g) as a light yellow solid.

Quelle