Reacción #927233

Ecuación de reacción

ammonium chloride

6-iodo-1-hexyne

sodium hydride

trifluoroacetamide

→

6-trifluoroacetamido-1-hexyne

Rendimiento 65.4%

Disolventes

ether

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe ether layer was dried over magnesium sulfate
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   Otrothe resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent)

Procedimiento

To a solution of sodium hydride (60% oil, 2.55 g, 63.6 mol) in DMF (50 ml), trifluoroacetamide (8.99 g, 79.6 mmol) was added portionwise as about 10 portions with ice cooling. Subsequently, a solution of 6-iodo-1-hexyne (3.31 g, 15.9 mmol) in DMF (15 ml) was added to the reaction mixture. The reaction mixture was stirred at room temperature for four hours. The reaction mixture was added with saturated aqueous ammonium chloride (100 ml) and ether (100 ml) for extraction. The ether layer was dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent) to afford 2.0 g of 6-trifluoroacetamido-1-hexyne (yield; 65.4%).

Fuente