Phenacyl bromide → 4-Phenyl-1,3-oxazole

A solution of phenacyl bromide (4 g, 20.1 mmol) and ammonium formate (4.4 g, 70.35 mmol) in formic acid (20 mL) was refluxed for 5 h. The deep red mixture was cooled to r.t., diluted with water and basified with dilute sodium hydroxide solution. This was extracted with ethyl acetate (×3), then the combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh), eluting with 20% ethyl acetate-petroleum ether, to afford 4-phenyloxazole (1 g, 34%) as a pale yellow oil which solidifies at −20° C.

1. extractionThis was extracted with ethyl acetate (×3)
2. washthe combined organic layers were washed with water and brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by column chromatography on silica gel (60-120 mesh)
6. washeluting with 20% ethyl acetate-petroleum ether

ORDレコード

ord-3453bd071969401f831ba76e5a9d13af

出典データセット

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08604029B2