Reaction #84916

Reaction equation

4-{5-chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine

pyridinium hydrochloride

→

4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}pyridin-2(1H)-one

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated under reduced pressure and water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   workup.ADDITIONAfter addition of ethyl acetate and phase separation
4. 4
   Washthe organic phase was washed once with water
5. 5
   Dryingdried (sodium sulphate)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   OtherThe crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures)

Procedure

550 mg (purity 41%, 0.71 mmol) of 4-{5-chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine and 20 eq. of pyridinium hydrochloride were reacted according to General Method 3A. The reaction mixture was concentrated under reduced pressure and water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate and dichloromethane/methanol mixtures). Yield: 141 mg (purity 91%, 59% of theory)

Source