反応 #2307975

反応方程式

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

収率 62.6%

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

収率 62.6%

溶媒

toluene

toluene

toluene

反応条件

後処理

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

実験手順

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).

出典