Reaction #2200600

Reaction equation

sodium methoxide

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

→

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

Solvents

methanol

ethyl acetate

methanol

Conditions

Workup

1. 1
   Washwashed with water
2. 2
   workup.ADDITIONTo the aqueous layer was added brine solution
3. 3
   Extractionwas extracted with ethyl acetate
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated to dryness

Procedure

A solution of methyl 3-chloro-6-(chloromethyl)pyridine-2-carboxylate 1-oxide (1.50 g, 6.35 mmol) in methanol (15 mL) was cooled to 0° C. A 25% solution of sodium methoxide in methanol (1.52 mL) was added and the mixture stirred at room temperature for 6 days. The reaction mixture was diluted with ethyl acetate and washed with water. To the aqueous layer was added brine solution and was extracted with ethyl acetate. The organic layers were combined, dried (MgSO4), filtered and concentrated to dryness to give crude methyl 3-chloro-6-(methoxymethyl)pyridine-2-carboxylate 1-oxide (1.14 g, 4.92 mmol) as a yellow oil; 1H NMR (CDCl3): δ 7.50 (d, 1H), 7.40 (d, 1H), 4.60 (s, 2H), 4.10 (s, 3H), 3.50 (s, 3H).

Source