Sodium hydride → HCID 22621552, compound

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.

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

ORD record

ord-384dc0588c3a4110bb2ac552d3f403b7

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265569B1