Réaction #1244253

Équation de réaction

triphenylphosphine

Compound 5c

2-(2-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-ethoxy)-ethanol

carbon tetrabromide

pyridine

→

compound 6c

Rendement 83.2%

(2-{2-[2-(2-Bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-tert-butyl-dimethyl-silane

Rendement 83.2%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreAfter standard workup with dichloromethane, the residue was purified by silica gel column chromatography (20% ethyl acetate in hexane)

Mode opératoire

Compound 5c (680 mg, 2.20 mmol) and carbon tetrabromide (947 mg, 2.86 mg) were dissolved in dichloromethane (20 ml). The solution was cooled down to 0° C. with an ice bath and pyridine (2.0 ml) was added followed by triphenylphosphine (749 mg, 0.286 mmol). The solution was stirred at 0° C. for half an hour and at room temperature for 2 hours. After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (20% ethyl acetate in hexane) to afford compound 6c (680 mg, 79.6%): 1H NMR δ 3.79 (m, 4H), 3.66 (m, 8H), 3.56 (t, 2H), 3.47 (t, 2H), 0.89 (s, 9H), 0.07 (s, 6H).

Source