Reaction #595337

Reaction equation

compound

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

thionyl chloride

→

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

Conditions

Workup

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

Procedure

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