Реакция #318378

Уравнение реакции

3,4,5-trimethoxybenzyl chloride

tert.-butyl lithium

water

( a )

2-(3,4,5-trimethoxyphenylmethyl)-1,3-dithiane

→

2,2-bis(3,4,5-trimethoxyphenylmethyl)-1,3-dithiane

Растворители

tetrahydrofuran

pentane

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added, over a period of 20 minutes
2. 2
   ЭкстракцияThe resultant slurry was then extracted with a mixture of ethyl acetate and water
3. 3
   Другоеdried
4. 4
   ДругоеThe organic layer was then evaporated
5. 5
   Промывкаthe crude product was washed with diethyl ether
6. 6
   Другоеto yield a solid

Методика

To a solution of 46.3 g of the compound prepared in (a) above in 230 ml of tetrahydrofuran at 0° C. was added, over a period of 20 minutes, 99.6 ml of a 1.7M solution of tert.-butyl lithium in pentane. The resultant mixture was then stirred for 20 minutes, after which time 34.9 g of 3,4,5-trimethoxybenzyl chloride in 150 ml of tetrahydrofuran at 0° C. was added over a period of 15 minutes. The reaction mixture was then stirred for 45 minutes, while the temperature was maintained at 0° C., and then 100 ml of water was carefully added. The resultant slurry was then extracted with a mixture of ethyl acetate and water and dried. The organic layer was then evaporated and the crude product was washed with diethyl ether to yield a solid.

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