Reaction #1061180

Reaction equation

methyl benzoylformate

4-dimethylamino-2-butynylamine

methanol

sodium hydroxide

→

N-(4-dimethylamino-2-butynyl)benzoylformamide

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe extract was washed with brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Otherevaporated in vacuo
5. 5
   OtherThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent

Procedure

A solution of methyl benzoylformate (0.50 g) and 4-dimethylamino-2-butynylamine (0.38 g) in methanol (5 ml) was refluxed for 3 hours. To the reaction mixture was added 1N aqueous solution of sodium hydroxide and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent to give N-(4-dimethylamino-2-butynyl)benzoylformamide (0.39 g).

Source