Réaction #1244252

ord-bc1182f303b44d2eb06e98753e7b1824

Équation de réaction

CCN(CC)CC
triethyl amine
OCCOCCOCCOCCO
Tetraethylene glycol
CC(C)(C)[Si](C)(C)Cl
TBDMSCl
CC(C)(C)[Si](C)(C)OCCOCCOCCOCCO
5c
Rendement 42.0%
CC(C)(C)[Si](C)(C)OCCOCCOCCOCCO
2-(2-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-ethoxy)-ethanol
Rendement 42.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07807135B2uspto-grants-2010_10