Reaktion #2307975

Reaktionsgleichung

Mesylate

6-{2-[2-(2-{2-[2-(2-methylsulfonylethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

NaH

diethylene glycol monomethyl ether

→

compound 6

Ausbeute 62.6%

6-(2-{2-[2-(2-{2-[2-(2-methoxyethoxy)ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-hexanoic acid ethyl ester

Ausbeute 62.6%

Lösungsmittel

toluene

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGAfter stirring at room temperature over night
4. 4
   Sonstigethe reaction was quenched by the addition of 2 ml of methanol
5. 5
   Filtrationthe resultant solution was filtered through silica gel
6. 6
   EinengenThe filtrate was concentrated in vacuo
7. 7
   SonstigeAdditional purification by preparatory chromatography (silica gel, 19/3 chloroform/methanol)

Vorschrift

NaH (88 mg of a 60% dispersion in oil, 2.2 mmol) was suspended in anhydrous toluene (3 ml) under N2 and chilled to 0° C. Monodispersed diethylene glycol monomethyl ether (0.26 ml, 0.26 g, 2.2 mmol) that had been dried via azeotropic distillation with toluene was added. The reaction mixture was allowed to warm to room temperature and stirred for four hours, during which time the cloudy grey suspension became clear and yellow and then turned brown. Mesylate 5 (0.50 g, 1.0 mmol) in 2.5 ml dry toluene was added. After stirring at room temperature over night, the reaction was quenched by the addition of 2 ml of methanol and the resultant solution was filtered through silica gel. The filtrate was concentrated in vacuo and the FAB MS: m/e 499 (M+H), 521 (M+Na). Additional purification by preparatory chromatography (silica gel, 19/3 chloroform/methanol) provided the monodispersed compound 6 as a clear yellow oil (0.302 g 57%). FAB MS: m/e 527 (M+H), 549 (M+Na).

Quelle