Reaction #595348

Reaction equation

water

sodium hydride

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

chlorodimethyl ether

→

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

Solvents

THF

Conditions

Workup

1. 1
   workup.WAITat RT for 1 h
2. 2
   TemperatureThe reaction mixture is again cooled to 0° C.
3. 3
   workup.STIRRINGThe mixture is stirred at 0° C. for 10 min
4. 4
   workup.WAITat RT for 2 h
5. 5
   Extractionthe reaction mixture is extracted three times with in each case 25 ml of ethyl acetate
6. 6
   DryingThe combined organic phases are dried over magnesium sulfate
7. 7
   Otherthe solvent is removed on a rotary evaporator
8. 8
   OtherThe product obtained
9. 9
   Otheris used without further purification in the subsequent reaction

Procedure

1.32 g (7.54 mmol) of [2-(4-chlorophenyl)-1,3-oxazol-4-yl]methanol (Example 100A) are initially charged in 18.5 ml of dry THF and cooled to 0° C., and 0.33 g (8.29 mmol) sodium hydride (60% strength in mineral oil) are added. The mixture is stirred at 0° C. for 10 min and then at RT for 1 h. The reaction mixture is again cooled to 0° C., and 0.69 ml (9.04 mmol) of chlorodimethyl ether is added. The mixture is stirred at 0° C. for 10 min and then at RT for 2 h. 5 ml of water are then added, and the reaction mixture is extracted three times with in each case 25 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The product obtained is used without further purification in the subsequent reaction.

Source