Réaction #595337

Équation de réaction

compound

[2-Phenyl-5-(trifluoromethyl)-1,3-oxazol-4-yl]methanol

thionyl chloride

→

4-(Chloromethyl)-2-phenyl-5-(trifluoromethyl)-1,3-oxazole

Conditions de réaction

Traitement

1. 1
   ConcentrationAfter concentration
2. 2
   Autreon a rotary evaporator
3. 3
   Lavagewashed once with 5 ml of sat. aqueous sodium bicarbonate solution
4. 4
   SéchageThe organic phase is dried over magnesium sulfate
5. 5
   FiltrationAfter filtration
6. 6
   Autrethe solvent is removed on a rotary evaporator
7. 7
   AutreThe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 400:1→60:1)
8. 8
   AutreThis gives a light-brown solid

Mode opératoire

359 mg (1.137 mmol, 76% purity) of the compound from Example 23A are initially charged in 0.63 ml (8.64 mmol) of thionyl chloride. The reaction mixture is stirred at RT for 48 h. After concentration on a rotary evaporator, the residue is taken up in 10 ml of ethyl acetate and washed once with 5 ml of sat. aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate. After filtration, the solvent is removed on a rotary evaporator. The residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 400:1→60:1). This gives a light-brown solid.

Source