Reacción #595349

Ecuación de reacción

N,N-dimethylformamide

n-butyllithium

crude product

2-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole

water

→

2-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carbaldehyde

Disolventes

hexane

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to RT
2. 2
   workup.STIRRINGstirred at RT for another 1 h
3. 3
   ExtracciónThe mixture is extracted three times with in each case 10 ml of diethyl ether
4. 4
   SecadoThe combined organic phases are dried over magnesium sulfate
5. 5
   Otrothe solvent is removed on a rotary evaporator
6. 6
   OtroThe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 20:1→2:1)

Procedimiento

200 mg (0.91 mmol) of the crude product from Example 40A are initially charged in 3.5 ml of dry diethyl ether and cooled to −78° C. 0.63 ml (1.00 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added dropwise. The reaction mixture is stirred at −78° C. for 1 h. 0.21 ml (2.74 mmol) of N,N-dimethylformamide is then slowly added dropwise. The mixture is allowed to warm to RT and stirred at RT for another 1 h. The mixture is then poured into about 3 ml of water. The mixture is extracted three times with in each case 10 ml of diethyl ether. The combined organic phases are dried over magnesium sulfate and 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 20:1→2:1).

Fuente