Reaction #1244252

Reaction equation

triethyl amine

Tetraethylene glycol

TBDMSCl

→

5c

Yield 42.0%

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

Yield 42.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherAfter standard workup with dichloromethane, the residue was purified by silica gel column chromatography (50% ethyl acetate in hexane)

Procedure

Tetraethylene glycol, 4c (1.12 g, 5.77 mmol) and TBDMSCl (0.87 g, 5.77 mmol) were dissolved in dichloromethane (25 ml) followed by triethyl amine (1.46 g, 14.4 mmol). The solution was stirred at room temperature for 2 hours. After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (50% ethyl acetate in hexane) to afford 5c (744 mg, 42%): 1H NMR δ 3.66 (m, 16H), 2.51 (t, 1H, J=5.86 Hz), 0.89 (s, 9H), 0.07 (s, 6H).

Source