Реакция #2690

Уравнение реакции

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dithiole

n-Butyllithium

4-Methoxycarbonyl-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d')-bis-(1,3)-dioxole

→

pure product

Выход 44.0%

Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)-dithiole-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methanol

Выход 44.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   workup.ADDITIONwas added
3. 3
   Другоеto reach ambient temperature
4. 4
   Другоеthe mixture was quenched with saturated aqueous NaH2PO4
5. 5
   Другоеthe organic layer evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   Промывкаwashed with water
8. 8
   Сушкаdried (Na2SO4)
9. 9
   ДругоеThe product was purified by column chromatography (dichloromethane:heptane, 1:1)

Методика

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dithiole (2.86 g, 10 mmol; prepared according to WO-91/12024) was dissolved in anhydrous THF (75 mL) and cooled to -70° C. n-Butyllithium (4.4 mL, 2.5M in hexane) was added. The reaction mixture was allowed to reach ambient temperature. 4-Methoxycarbonyl-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d')-bis-(1,3)-dioxole (1.4 g, 5 mmol) was added as a solid. After 1 hour, the mixture was quenched with saturated aqueous NaH2PO4. The aqueous phase was discarded and the organic layer evaporated. The residue was dissolved in dichloromethane, washed with water and dried (Na2SO4). The product was purified by column chromatography (dichloromethane:heptane, 1:1) giving 1.8 g (44%) of pure product.

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