تفاعل #340320

معادلة التفاعل

sodium sulfite

(1-allylcyclobutoxy) (tert-butyl)dimethylsilane

H2O t-BuOH

NMO

→

3-(1-(tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

المذيبات

H2O

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction was stirred at RT
2. 2
   workup.WAITAfter 2 h
3. 3
   أخرىthe reaction
4. 4
   workup.STIRRINGthe reaction was stirred for another hour
5. 5
   استخلاصThe aqueous solution was extracted with ether (2×1 L)
6. 6
   تركيزThe combined organics were concentrated in vacuo

الإجراء التجريبي

To a 2 L round bottomed flask was added (1-allylcyclobutoxy) (tert-butyl)dimethylsilane (previous step) and H2O/t-BuOH (1:1, 1 L). NMO (32.68 g, 279 mmol) was added to the mixture. After stirring for 5 min the solution was found to be homogenous. Osmium tetroxide (1.00 g, 3.93 mmol) was added and the reaction was stirred at RT. After 2 h, TLC revealed the reaction to be complete. 500 mL of H2O and sodium sulfite (19.5 g, 155 mmol) were added and the reaction was stirred for another hour. The aqueous solution was extracted with ether (2×1 L). The combined organics were concentrated in vacuo to give 3-(1-(tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol, as a light yellow oil. The oil contained some t-BuOH, but was carried forward without further purification.

المصدر