تفاعل #1016

معادلة التفاعل

3,5-Dichloropyridine

LDA

sodium hydrogen carbonate

iodomethane

→

title compound

المردود 53.0%

3,5-Dichloro-4-methylpyridine

المردود 53.0%

المذيبات

THF

THF

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر