Reaktion #2317403

Reaktionsgleichung

methyl chloroacetate

methyl chloroacetate

sodium

10.2

(R,S)-4-Methyl-4-(4-(tetrahydropyran-2-yloxy)phenyl)-2,5-dioxoimidazolidine

potassium iodide

→

10.3

Ausbeute 71.0%

Methyl ((R,S)-4-methyl-4-(4-(tetrahydropyran-2-yloxy)phenyl)-2,5-dioxoimidazolidin-1-yl)acetate

Ausbeute 71.0%

Lösungsmittel

methanol

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturto reflux for 4 hours
5. 5
   workup.WAITto stand at room temperature overnight
6. 6
   workup.STIRRINGthe batch was stirred
7. 7
   Temperaturunder reflux for 4 hours
8. 8
   FiltrationThe precipitate was filtered off with suction
9. 9
   Einengenthe filtrate was concentrated
10. 10
    workup.DISSOLUTIONThe residue was dissolved in methylene chloride
11. 11
    Filtrationinsoluble matter was filtered off
12. 12
    Sonstigethe filtrate was chromatographed on silica gel

Vorschrift

230 mg (10 mmol) of sodium were dissolved in 25 ml of anhydrous methanol under argon. 2.9 g (10 mmol) of 10.2 were added. The mixture was heated to reflux with stirring for 2 hours. 1.66 g (10 mmol) of potassium iodide were then added and a solution of 0.975 ml (10 mmol) of methyl chloroacetate in 1.1 ml of anhydrous methanol was added dropwise in the course of 15 minutes. The mixture was heated to reflux for 4 hours and then allowed to stand at room temperature overnight. A further 0.195 ml (2 mmol) of methyl chloroacetate in 0.22 ml of anhydrous methanol were added and the batch was stirred under reflux for 4 hours. The precipitate was filtered off with suction and the filtrate was concentrated. The residue was dissolved in methylene chloride, insoluble matter was filtered off and the filtrate was chromatographed on silica gel using methylene chloride/ethyl acetate (9:1). 2.56 g (71%) of 10.3 were obtained.

Quelle