Réaction #46264

Équation de réaction

2-butoxy-2-oxoethanaminium chloride

triethylamine

diethyl oxalate

→

title material

Butyl N-[ethoxy(oxo)acetyl]glycinate

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe product mixture was cooled
2. 2
   Concentrationconcentrated under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in methylene chloride
4. 4
   Lavagewashed with two 4 L portions of water
5. 5
   SéchageThe organic fraction was dried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum
8. 8
   AutreCollection and concentration of appropriate fractions

Mode opératoire

A mixture of 2-butoxy-2-oxoethanaminium chloride (573.5 g, 3.42 mol), triethylamine (415 g, 4.1 mol), and diethyl oxalate (1.0 kg, 6.8 mol) in ethanol (7 L) was heated at 50° C. for 3 hours. The product mixture was cooled and concentrated under vacuum. The residue was dissolved in methylene chloride and washed with two 4 L portions of water. The organic fraction was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residual oil was subjected to column chromatography on silica gel eluting with heptane/ethyl acetate gradient. Collection and concentration of appropriate fractions provided the title material.

Source