反应 #1016

反应方程式

3,5-Dichloropyridine

LDA

sodium hydrogen carbonate

iodomethane

→

title compound

收率 53.0%

3,5-Dichloro-4-methylpyridine

收率 53.0%

溶剂

THF

THF

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction mixture stirred for a further 1.5 h at -70° C
2. 2
   其他the organic phase separated
3. 3
   干燥dried (MgSO4)
4. 4
   浓缩concentrated in vacuo

实验过程

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).

来源