Реакция #496190

Уравнение реакции

NaOH

tert-butyl(((5R,6S,6aS)-6-iodo-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)diphenylsilane

Bu3SnH

AIBN

→

viscous title compound

Выход 86.0%

tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane

Выход 86.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ПромывкаThis mixture was then finally washed with brine
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   СушкаThe organic layers were dried over anhydrous Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеPurification

Методика

A solution of tert-butyl(((5R,6S,6aS)-6-iodo-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)diphenylsilane (from step 6) (10.3 g, 0.0186 mol), Bu3SnH (5.9 mL, 0.0224 mol) and AIBN (5 mol %) in 120 mL anhydrous toluene was refluxed for 7 h. The reaction mixture was cooled to room temperature and 100 mL of 1N NaOH was added and stirred for one h. This mixture was then finally washed with brine and extracted with ethyl acetate. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Purification was performed by column chromatography using hexane and ethyl ether as a gradient mixture to give 6.8 g of viscous title compound in 86% yield.

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