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

Temperature

0 °C

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.

1. waitat RT for 1 h
2. temperatureThe reaction mixture is again cooled to 0° C.
3. stirringThe mixture is stirred at 0° C. for 10 min
4. waitat RT for 2 h
5. extractionthe reaction mixture is extracted three times with in each case 25 ml of ethyl acetate
6. dry with materialThe combined organic phases are dried over magnesium sulfate
7. customthe solvent is removed on a rotary evaporator
8. customThe product obtained
9. customis used without further purification in the subsequent reaction

ORD record

ord-6f606332dd1d4eaab6be96d2696bb75d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09095582B2