Hydrochloric Acid → 4-[(Methoxymethoxy)methyl]-2-phenyl-1,3-oxazole-5-carbaldehyde

Temperatur

-78 °C

To a mixture of 4-methoxymethoxymethyl-2-phenyloxazole (10.86 g) and diethyl ether (300 mL) was dropwise added a solution (1.6 M, 37 mL) of n-butyl lithium in hexane at −78° C., and the mixture was stirred at −78° C. for 1.5 hrs. A solution (10 mL) of N,N-dimethylformamide (6.50 g) in diethyl ether was added to the reaction mixture and the reaction mixture was allowed to warm to room temperature with stirring for 2 hrs. Dilute hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (6.45 g, 53%) of 4-methoxymethoxymethyl-2-phenyl-5-oxazolecarbaldehyde from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 51-52° C.

1. temperatureto warm to room temperature
2. stirringwith stirring for 2 hrs
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated

ORD-Eintrag

ord-8b189d13eda648a286070feb927bc26f

Quelldatensatz

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07238716B2