Reaction #1603

Reaction equation

ammonium chloride

NaH

pyridinone

hexane ethyl acetate

1-bromo-2-pentyne

→

5-(4-chlorophenyl)-1-(2-pentyn-1-yl)-2-pyridinone

Solvents

DMF

Conditions

Workup

1. 1
   workup.WAITThe resulting mixture was kept at 0° C. during one half hour
2. 2
   ExtractionThe aqueous suspension was extracted with ether (3×100 ml)
3. 3
   Washthe combined ether layers washed with brine
4. 4
   Otherdried
5. 5
   Otheryielding the crude product

Procedure

To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml) and the combined ether layers washed with brine and dried, yielding the crude product. After column chromatography (silica gel, hexane:ethyl acetate 8:2) the product was obtained as a white amorphous solid.

Source