Reaction #595353

Reaction equation

compound

Methyl 2-(4-chlorophenyl)-4-(hydroxymethyl)-1,3-oxazole-5-carboxylate

thionyl chloride

→

Methyl 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole-5-carboxylate

Conditions

Workup

1. 1
   OtherThe excess thionyl chloride is removed under reduced pressure
2. 2
   WashThe mixture is washed once with 2 ml of sat. aqueous sodium bicarbonate solution
3. 3
   DryingThe organic phase is dried over magnesium sulfate
4. 4
   Otherthe solvent is removed under reduced pressure
5. 5
   OtherThe product obtained
6. 6
   Otheris used without further purification in the subsequent reactions

Procedure

100 mg (0.43 mmol) of the compound from Example 44A, together with 0.24 ml (3.24 mmol) of thionyl chloride, are stirred at RT for 8 h. The excess thionyl chloride is removed under reduced pressure and the residue is taken up in about 5 ml of ethyl acetate. The mixture is washed once with 2 ml of sat. aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The product obtained is used without further purification in the subsequent reactions.

Source