Réaction #927237

Équation de réaction

sodium hydride

trifluoroacetamide

8-iodo-1-octyne

ammonium chloride

→

8-trifluoroacetamido-1-octyne

Rendement 79.5%

Solvants

DMF

DMF

ether

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added portionwise with ice cooling
2. 2
   SéchageThe ether layer was dried over magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   Autrethe resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent)
5. 5
   Autrecrystallized from hexane

Mode opératoire

To a solution of sodium hydride (60% oil, 9.82 g, 245 mmol) in DMF (200 ml), trifluoroacetamide (34.7 g, 307 mmol) divided into 10 portion was added portionwise with ice cooling. Then, the reaction mixture was added with a solution of 8-iodo-1-octyne (14.5 g, 61.4 mmol) in DMF (60 ml), and stirred at room temperature for two hours. The reaction mixture was added with saturated aqueous ammonium chloride (400 ml) and ether (400 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), and crystallized from hexane to afford 10.8 g of 8-trifluoroacetamido-1-octyne (yield; 79.3%).

Source