Formamide → 4-Phenyl-1,3-oxazole

HRID 1944709

反応式

HRID 1944709 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:11]([NH2:13])=[O:12]>C(OCC)(=O)C.O>[C:5]1([C:3]2[N:13]=[CH:11][O:12][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 713FormamideHCID 6259Phenacyl bromide

生成物 1

HCID 5892794-Phenyl-1,3-oxazole収率 39.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

Bromoacetophenone (595 mg, 2.99 mmol) and formamide (1781 μl, 44.8 mmol) were combined and heated at 130° C. for 90 min. The reaction was cooled then dilute with ethyl acetate and water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrate was purified by chromatography on a Biotage 25M column using a 5-8% ethyl acetate in heptane gradiant to yield 4-phenyl-oxazole (170 mg, 1.17 mmol). TLC (5% ethyl acetate in heptane) of product: Rf=0.28.

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by chromatography on a Biotage 25M column

出典と根拠

ORDレコード
ord-052b546579ef47e1bf8a809b91d1baf8
出典データセット
uspto-grants-2013_03
特許番号
US08394858B2

関連ノート

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