2-(Trimethylsilyl)ethanol → HCID 19756384, compound

Participants

Reaction Steps

Potassium t-butoxide (25.8 g) was added portionwise over 20 minutes to a solution of 2-(trimethylsilyl)ethanol (20.8 g) and 2-chloro-5-nitropyridine (27.8 g) in DMF (170 ml). The mixture was stirred for 18 hours and then poured into ice-water (900 ml). The mixture was extracted with ethyl acetate (3×300 ml) and the extracts were washed with water (200 ml), followed by saturated sodium chloride solution (200 ml) and dried (MgSO4). Volatile material was removed by evaporation to give 5-nitro-2-[2-(trimethylsilyl)ethoxy]pyridine (34.9 g) as an oil; NMR: 0.05(s,9H), 1.1-1.2(m,2H), 4.45-4.55(m,2H), 6.75(d,1H), 8.3(dd,1H), 9.05(d,1H).

Provenance & Evidence