Реакция #1016

Уравнение реакции

3,5-Dichloropyridine

LDA

sodium hydrogen carbonate

iodomethane

→

title compound

Выход 53.0%

3,5-Dichloro-4-methylpyridine

Выход 53.0%

Растворители

THF

THF

dichloromethane

Условия реакции

Обработка

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

Методика

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).

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