تفاعل #2690

معادلة التفاعل

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

المردود 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

المردود 44.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared
2. 2
   workup.ADDITIONwas added
3. 3
   أخرىto reach ambient temperature
4. 4
   أخرىthe mixture was quenched with saturated aqueous NaH2PO4
5. 5
   أخرىthe organic layer evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   غسيلwashed with water
8. 8
   تجفيفdried (Na2SO4)
9. 9
   أخرىThe product was purified by column chromatography (dichloromethane:heptane, 1:1)

الإجراء التجريبي

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.

المصدر