반응 #1016

반응 방정식

3,5-Dichloropyridine

LDA

sodium hydrogen carbonate

iodomethane

→

title compound

수율 53.0%

3,5-Dichloro-4-methylpyridine

수율 53.0%

용매

THF

THF

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture stirred for a further 1.5 h at -70° C
2. 2
   기타the organic phase separated
3. 3
   건조dried (MgSO4)
4. 4
   농축concentrated in vacuo

실험 절차

3,5-Dichloropyridine (2.04 g, 13.5 mmol) in THF (5 ml) was added dropwise to a solution of LDA [prepared from diisopropylamine (1.9 ml, 13.5 mmol) and n-butyllithium (1.6M, 8.4 ml, 13.5 mmol)] in THF (25 ml) at -70° C. After stirring at this temperature for 5 min, iodomethane (0.85 ml, 13.5 mmol) was added and the reaction mixture stirred for a further 1.5 h at -70° C. Saturated sodium hydrogen carbonate solution (20 ml) and dichloromethane (20 ml) was added and the organic phase separated, dried (MgSO4), and concentrated in vacuo. The residue was subjected to chromatography (SiO2 ; Et2O-hexane, 1:3) to afford the title compound (1.16 g) as a pale yellow solid; δH (CDCl3) 2.46 (3H, s, Me), and 8.36 (2H, s, pyridine H2, H6).

출처