تفاعل #2307975

معادلة التفاعل

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

المردود 62.6%

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

المردود 62.6%

المذيبات

toluene

toluene

toluene

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر