Reaktion #2691

Reaktionsgleichung

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

Lösungsmittel

benzene

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeultrasound for 25 min.
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigeAfter purification by preparative HPLC 130.0 mg (21%)) of the pure product
7. 7
   Sonstigewas obtained

Vorschrift

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).

Quelle