Reaktion #553661

Reaktionsgleichung

trifluoromethanesulfonyl chloride

trifluoromethanesulfonyl chloride

sodium bis(trimethylsilyl)amide

HCl

sodium bis(trimethylsilyl)amide

compound

5-[Cyano(dihydro-2(3H)-furanylidene)methyl]-4-(2-methylpropyl)-2-(difluoromethyl)6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester

→

desired product

Ausbeute 24.0%

5[Cyano(3,3-dichlorodihydro-2(3H)-furanylidene)methyl]-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester

Ausbeute 24.0%

Lösungsmittel

—

hexanes

ethyl acetate

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl ether
2. 2
   WaschenThe combined organic layers were washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationan filtered
5. 5
   Sonstigeto give 1.5 g of crude orange oil

Vorschrift

A 100 mL round-bottomed flask was charged with 1.5 g (3.6 mmol) of the compound of Example 2 and 20 mL anhydrous THF. The solution was cooled to -70° C. and 3.6 mL sodium bis(trimethylsilyl)amide (1.0 M solution in THF) was added via syringe. After 5 minutes, 0.6 g (3.6 mmol) trifluoromethanesulfonyl chloride was added. After 15 minutes an additional 3.6 mL sodium bis(trimethylsilyl)amide was added followed by additional 0.6 g trifluoromethanesulfonyl chloride. After stirring one hour at -70° C., the reaction solution was poured into dilute HCl and extracted with ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, an filtered to give 1.5 g of crude orange oil. Chromatography using 20% ethyl acetate in hexanes yielded 0.42 g of the desired product as a yellow oil, a 24% yield. nD25 1.4920.

Quelle