Réaction #4536

Équation de réaction

methyl acetate

3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine

p-toluenesulfonic acid

→

5-dichloromethyl-3-hydroxymethyl-2-phthalimidopyrazine

Rendement 54.0%

Solvants

methanol

methanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated to the boil
2. 2
   workup.DISTILLATIONwas slowly distilled off in the course of 5 hours
3. 3
   AutreThe mixture was then evaporated down to one-third of its total volume
4. 4
   Autrethe precipitated crystals were isolated
5. 5
   Autrerecrystallized from ethyl acetate

Mode opératoire

A mixture of 15 g (0.04 mole) of 3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine, 150 ml of methanol and 0.15 g of p-toluenesulfonic acid was heated to the boil, and a mixture of methanol and methyl acetate was slowly distilled off in the course of 5 hours. The mixture was then evaporated down to one-third of its total volume, and the precipitated crystals were isolated, and recrystallized from ethyl acetate. 7.18 g (54%) of 5-dichloromethyl-3-hydroxymethyl-2-phthalimidopyrazine of melting point 188°-189° C. were obtained. 1H-NMR (CDCl3 270 MHz): δ4.7 (s, 2H), 6.9 (s, 1H), 8.1 (m, 4H), 9.1 (s, 1H).

Source