Reaktion #553660

Reaktionsgleichung

HCl

trifluoromethanesulfonyl chloride

trifluoromethanesulfonyl chloride

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 27.0%

2-(Difluoromethyl)-5-[(3-chlorodihydro-2(3H)-furanylidene) cyanomethyl]-6-(trifluoromethyl)-4-(2-methylpropyl)-3-pyridinecarboxylic acid, methyl ester

Ausbeute 27.0%

Lösungsmittel

—

hexanes

ethyl acetate

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl ether
2. 2
   TrocknenThe combined organic layers were dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give 1.3 g of crude product

Vorschrift

A 100 mL round-bottomed flask was charged with 1.2 g (2.9 mmol) of the compound of Example 2 and 30 mL anhydrous THF and cooled to -70° C. Then 2.9 mL sodium bis(trimethylsilyl)amide (1.0 M solution in THF) was added. After 5 minutes, 0.48 g (2.9 mmol) trifluoromethanesulfonyl chloride was added. To the reaction mixture was added 0.25 g additional trifluoromethanesulfonyl chloride. The reaction mixture was poured into dilute HCl and extracted with ethyl ether. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 1.3 g of crude product. Chromatography using 15% ethyl acetate in hexanes yielded 0.34 g of the desired product, as a yellow oil, a 27% yield. nD25 1.4860.

Quelle