Reaktion #927233

Reaktionsgleichung

ammonium chloride

6-iodo-1-hexyne

sodium hydride

trifluoroacetamide

→

6-trifluoroacetamido-1-hexyne

Ausbeute 65.4%

Lösungsmittel

ether

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle