Reaction #595336

Reaction equation

sodium hydroxide

lithium aluminum hydride

4-methylmorpholine

ethyl chloroformate

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

→

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

Solvents

water

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture is stirred overnight
2. 2
   Temperatureto warm to RT
3. 3
   TemperatureThe mixture is then once more cooled to 0° C.
4. 4
   workup.STIRRINGThe mixture is then stirred at RT overnight
5. 5
   FiltrationAfter filtration
6. 6
   Otherthe solvent is removed on a rotary evaporator
7. 7
   OtherThe residue is used without further purification in the subsequent reaction

Procedure

500 mg (1.94 mmol) of 2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic acid are dissolved in 40 ml of dry THF and cooled to −10° C. 197 mg (1.94 mmol) of 4-methylmorpholine and 211 mg (1.94 mmol) of ethyl chloroformate are added. The reaction solution is stirred at −10° C. for 1 h. 3.9 ml (3.89 mmol) of a 1 M solution of lithium aluminum hydride in THF are then slowly added dropwise. The reaction mixture is stirred overnight and slowly allowed to warm to RT. The mixture is then once more cooled to 0° C., and 0.6 ml of water and 1.2 ml of 1 N aqueous sodium hydroxide solution are added carefully. The mixture is then stirred at RT overnight. After filtration, the solvent is removed on a rotary evaporator. The residue is used without further purification in the subsequent reaction.

Source