Reaction #595340

Reaction equation

lithium aluminum hydride

compound

Ethyl 2-(4-chloro-3-methylphenyl)-1,3-oxazole-4-carboxylate

water

sodium hydroxide

→

[2-(4-Chloro-3-methylphenyl)-1,3-oxazol-4-yl]methanol

Solvents

THF

THF

Conditions

Workup

1. 1
   TemperatureThe reaction solution is then once more cooled to 0° C.
2. 2
   workup.STIRRINGThe mixture is stirred at RT overnight
3. 3
   OtherThe precipitate formed
4. 4
   Filtrationis filtered off
5. 5
   Othera rotary evaporator
6. 6
   OtherThe residue is used without further purification in the subsequent reaction

Procedure

46 mg (1.22 mmol) of lithium aluminum hydride are initially charged in 8.0 ml of THF and cooled to 0° C. A solution of 161 mg (0.61 mmol) of the compound from Example 26A in 2.5 ml of THF is then added dropwise. The mixture is stirred at RT for 2 h. The reaction solution is then once more cooled to 0° C., and 0.2 ml of water and 0.4 ml of 1 N aqueous sodium hydroxide solution are added. The mixture is stirred at RT overnight. The precipitate formed is filtered off, and the filtrate is freed from the solvent using a rotary evaporator. The residue is used without further purification in the subsequent reaction.

Source