Reaction #927233

Reaction equation

ammonium chloride

6-iodo-1-hexyne

sodium hydride

trifluoroacetamide

→

6-trifluoroacetamido-1-hexyne

Yield 65.4%

Solvents

ether

DMF

DMF

Conditions

Workup

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

Procedure

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%).

Source