Reaktion #987167

Reaktionsgleichung

2-ethyl-4-(hydroxymethyl)pyridine

dibromotriphenylphosphorane

→

2-ethyl-4-(bromomethyl)pyridine

Ausbeute 14.2%

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 3×50 ml of water
2. 2
   TrocknenThe organic phase is dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated to dryness under reduced pressure
5. 5
   SonstigeThe residue thus obtained
6. 6
   Sonstigeis purified by flash chromatography
7. 7
   Wascheneluted with a mixture (cyclohexane/ethyl acetate) (9/1) (v/v), at a flow rate of 8 ml/minute
8. 8
   EinengenThe fractions between 80 and 120 ml are concentrated under reduced pressure

Vorschrift

A solution of 0.3 g of 2-ethyl-4-(hydroxymethyl)pyridine in 3.5 ml of dichloromethane is added dropwise to a solution of 1.25 g of dibromotriphenylphosphorane in 4 ml of dichloromethane, under an inert atmosphere of argon at a temperature in the region of 0° C. The mixture is stirred to a temperature in the region of 20° C. over about 1 hour. The reaction medium is taken up in 50 ml of dichloromethane and then washed with 3×50 ml of water. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. The residue thus obtained is purified by flash chromatography using a cartridge 20 mm in diameter packed with 10 g of 20-40 μm conditioned silica, and then eluted with a mixture (cyclohexane/ethyl acetate) (9/1) (v/v), at a flow rate of 8 ml/minute. The fractions between 80 and 120 ml are concentrated under reduced pressure. 0.062 g of 2-ethyl-4-(bromomethyl)pyridine is thus obtained.

Quelle