تفاعل #2200601

معادلة التفاعل

methyl 3-chloro-6-(methoxymethyl)pyridine-2-carboxylate 1-oxide

phosphorus oxychloride

→

methyl 3,4-dichloro-6-(methoxymethyl)pyridine-2-carboxylate

المردود 98.3%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 4 hours
2. 2
   تركيزwas concentrated to dryness in vacuo
3. 3
   workup.ADDITIONThe residue was diluted with ethyl ether
4. 4
   غسيلcarefully washed with saturated NaHCO3 solution
5. 5
   أخرىThe organic layer was separated
6. 6
   استخلاصthe aqueous layer was extracted with ethyl ether
7. 7
   تجفيفthe solution was dried (MgSO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated to dryness

الإجراء التجريبي

To a solution of methyl 3-chloro-6-(methoxymethyl)pyridine-2-carboxylate 1-oxide (1.64 g, 7.08 mmol) in acetonitrile (28 mL) was added phosphorus oxychloride (1.32 mL, 14.16 mmol) and the mixture stirred at reflux for 4 hours. After cooling to room temperature the mixture was concentrated to dryness in vacuo. The residue was diluted with ethyl ether and carefully washed with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with ethyl ether. After the organic layers were combined, the solution was dried (MgSO4), filtered and concentrated to dryness to give crude methyl 3,4-dichloro-6-(methoxymethyl)pyridine-2-carboxylate (1.74 g) as a yellow oil; 1H NMR (CDCl3): δ 7.70 (s, 1H), 4.60 (s, 2H), 4.00 (s, 3H), 3.40 (s, 3H).

المصدر