Potassium Carbonate → 4-(4-Methoxyphenyl)-1,2-oxazole

Temperature

80 °C

A round-bottomed flask was charged with potassium carbonate (1.45 g, 10.5 mmol) and ethanol (14 ml). To this mixture was added hydroxylamine hydrochloride (730 mg, 10.5 mmol), and 2-(4-methoxyphenyl)-malondialdehyde (1.25 g, 7.00 mmol). The reaction mixture was heated at about 80° C. for about three hours. The reaction mixture was then concentrated in vacuo to approximately one-quarter volume and partitioned between water and ethyl acetate. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to a dark oil. This crude material was purified by column chromatography (10% ethyl acetate/hexanes) to afford 1.06 g (86% yield) of the desired product. LRMS ([M−H]−)=174.1.

1. concentrationThe reaction mixture was then concentrated in vacuo to approximately one-quarter volume
2. custompartitioned between water and ethyl acetate
3. extractionThe mixture was extracted with ethyl acetate
4. dry with materialthe combined organic extracts were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo to a dark oil
7. customThis crude material was purified by column chromatography (10% ethyl acetate/hexanes)

ORD record

ord-3bd9c5cb47c7453382c873a17542b3ba

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06706743B2