Reaktion #169512

Reaktionsgleichung

5-(1-bromoethyl)-2-(trichloromethyl)pyridine

sodium thiomethoxide

→

5-[1-(methylthio)ethyl]-2-(trichloromethyl)pyridine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent ethanol was then removed under a reduced pressure
2. 2
   SonstigeThe two phases were separated
3. 3
   Trocknenthe organic layer was dried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified on silica gel using 5 percent EtOAc in hexane

Vorschrift

A solution of 5-(1-bromoethyl)-2-(trichloromethyl)pyridine (A) (0.95 g, 3.14 mmol) in ethanol (15 mL) was treated with sodium thiomethoxide (0.44 g, 6.29 mmol) portionwise at 0° C. The mixture was stirred at room temperature overnight. The solvent ethanol was then removed under a reduced pressure and the residue was re-taken into CH2Cl2 and brine. The two phases were separated and the organic layer was dried over anhydrous Na2SO4, filtered, concentrated. The residue was purified on silica gel using 5 percent EtOAc in hexane to give 0.57 g of the partially pure 5-[1-(methylthio)ethyl]-2-(trichloromethyl)pyridine (B) in 67 percent crude yield. GC-MS: mass calcd for C9H10Cl3NS [M]+ 269. Found 269.

Quelle