반응 #2307975

반응 방정식

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

수율 62.6%

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

수율 62.6%

용매

toluene

toluene

toluene

반응 조건

후처리

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

실험 절차

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).

출처