Reacción #2690

Ecuación de reacción

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

Rendimiento 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

Rendimiento 44.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   workup.ADDITIONwas added
3. 3
   Otroto reach ambient temperature
4. 4
   Otrothe mixture was quenched with saturated aqueous NaH2PO4
5. 5
   Otrothe organic layer evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   Lavadowashed with water
8. 8
   Secadodried (Na2SO4)
9. 9
   OtroThe product was purified by column chromatography (dichloromethane:heptane, 1:1)

Procedimiento

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.

Fuente