Reaction #5614

Reaction equation

5-benzyloxy-2-hydroxymethyl-4-pyridone

thionyl chloride

→

5-benzyloxy-2-chloromethyl-4-pyridone

Solvents

benzene

Conditions

Workup

1. 1
   workup.STIRRINGAfter being stirred at the same temperature for 30 minutes
2. 2
   Temperaturethe mixture was refluxed for 4 hours
3. 3
   FiltrationThe precipitate was collected by filtration
4. 4
   Washwashed with benzene
5. 5
   Otherdried under reduced pressure

Procedure

To a suspension of 5-benzyloxy-2-hydroxymethyl-4-pyridone (33 g) in benzene (500 ml) was added thionyl chloride (28.4 ml) at ambient temperature under stirring. After being stirred at the same temperature for 30 minutes, the mixture was refluxed for 4 hours. The resulting mixture was cooled to ambient temperature. The precipitate was collected by filtration, washed with benzene and dried under reduced pressure to give 5-benzyloxy-2-chloromethyl-4-pyridone (41.5 g).

Source