Reaktion #1951045

Reaktionsgleichung

nicotinic acid

sodium bicarbonate

tetrabutylammonium sulfate

chloromethylchlorosulfone

→

chloromethyl pyridine-3-carboxylate

Ausbeute 25.5%

Lösungsmittel

dichloromethane

dichloromethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated under reduced pressure to a yellow oil, which
6. 6
   workup.DISSOLUTIONwas dissolved in dichloromethane
7. 7
   Filtrationfiltered through a silica plug
8. 8
   SonstigeRemoval of the solvent under reduced pressure

Vorschrift

A mixture of nicotinic acid (200 mg, 1.6 mmol), sodium bicarbonate (540 mg, 6.4 mmol), and tetrabutylammonium sulfate (54 mg, 0.16 mmol) was dissolved in a mixture of 4 ml of dichloromethane and 4 ml of water, and cooled to 0° C. To this stirred mixture was added chloromethylchlorosulfone (165 μl, 1.6 mmol) in 1 ml of dichloromethane, and the mixture was allowed to warm to room temperature, stirring overnight. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to a yellow oil, which was dissolved in dichloromethane and filtered through a silica plug. Removal of the solvent under reduced pressure provided chloromethyl pyridine-3-carboxylate (70 mg).

Quelle