반응 #1473828

반응 방정식

ammonium chloride

6-iodo-1-hexyne

sodium hydride

trifluoroacetamide

→

6-trifluoroacetamido-1-hexyne

수율 65.4%

용매

ether

DMF

DMF

반응 조건

후처리

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

실험 절차

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%). Melting point: 41.0-42.5° C.

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