تفاعل #217071

معادلة التفاعل

3-(5-hexenyl)-1-methylthymine

4-methylmorpholine-N-oxide

water

sodium hydrosulfite

→

3-(5,6-dihydroxyhexyl)-1-methylthymine

المردود 89.0%

المذيبات

t-butanol

acetone

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with 20% ethanol-dichloromethane (4×40 ml)
2. 2
   تجفيفThe combined organic layers were dried over sodium sulfate
3. 3
   أخرىthe solvents were evaporated under vacuum
4. 4
   أخرىto give a solid residue
5. 5
   أخرىThe solid was recrystallized (ethanol)

الإجراء التجريبي

A solution of 3-(5-hexenyl)-1-methylthymine (2.00 g, 9 mmol), 4-methylmorpholine-N-oxide (1.17 mg, 10 mmol), and osmium tetroxide (0.15 ml of a 2.5% solution in t-butanol) in acetone (15 ml) and water (10 ml) was stirred for 20 hours. Saturated aqueous sodium hydrosulfite solution (10 ml) was added and after 15 minutes of stirring, the mixture was extracted with 20% ethanol-dichloromethane (4×40 ml). The combined organic layers were dried over sodium sulfate and the solvents were evaporated under vacuum to give a solid residue. The solid was recrystallized (ethanol) to give 3-(5,6-dihydroxyhexyl)-1-methylthymine (2.00 g, 89% yield).

المصدر