反应 #2691

反应方程式

t-Butyllitium

TMEDA

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)dioxol-4-yl)methanol

diethyl carbonate

→

Bis-(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)-mono-(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)methanol

溶剂

benzene

benzene

反应条件

后处理

1. 1
   其他ultrasound for 25 min.
2. 2
   其他The organic layer was separated
3. 3
   洗涤washed with water
4. 4
   干燥dried (Na2SO4)
5. 5
   其他evaporated
6. 6
   其他After purification by preparative HPLC 130.0 mg (21%)) of the pure product
7. 7
   其他was obtained

实验过程

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)dioxol-4-yl)methanol (0.50 g, 0.61 mmol) was dissolved in dry benzene (6.0 mL) under an atmosphere of argon. t-Butyllitium (2.44 mL, 1.5M in pentane) and TMEDA (0.545 mL, 3.66 mmol) were added. The reaction mixture was subjected to ultrasound for 25 min. and was then slowly added to a solution of diethyl carbonate (7.2 mL, 59.4 mmol) in dry benzene (16 mL). After stirring for 1.5 h, aqueous NaH2PO4 (50 mL) was added. The organic layer was separated, washed with water, dried (Na2SO4) and evaporated. After purification by preparative HPLC 130.0 mg (21%)) of the pure product was obtained. 1H NMR (CDCl3, 300 MHz) δ: 4.98 (s, 1H), 4.28-4.37 (m, 6H), 1.48-1.79 (m, 36H), 1.46 (t, 6H, J 7.0 Hz), 1.38 (t, 3H, J 7.0 Hz).

来源