Diazomethane → 1-(2-(4-Fluorophenyl)oxazol-4-yl)ethanone

HRID 1397420ノート

反応式

HRID 1397420 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[N+](=[CH2:17])=[N-]>C(Cl)(Cl)Cl.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13](=[O:14])[CH3:17])[N:12]=2)=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 9550DiazomethaneHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

生成物 1

HCID 673225581-(2-(4-Fluorophenyl)oxazol-4-yl)ethanone収率 58%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6212Chloroform溶媒

実験手順

A solution of 2-(4-fluorophenyl)oxazole-4-carbaldehyde (400 mg, 2.09 mmol) in dry chloroform (5 mL) was cooled to 0° C. and a freshly prepared solution of diazomethane in ether (20 mL) was added. The reaction mixture was stirred for 1 h and quenched with 10% aqueous NaHCO3 solution. The crude product was extracted with CH2Cl2 and the combined extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5-8% EtOAc in petroleum ether) to afford 1-(2-(4-fluorophenyl)oxazol-4-yl)ethanone (250 mg, yield 58%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 8.12-8.09 (m, 2H), 7.21-7.17 (t, J=8.7 Hz, 2H), 2.60 (s, 3H). MS (ESI) m/z: Calculated for C11H8FNO2: 205.05. found: 205.9 (M+H)+.

後処理

  1. customquenched with 10% aqueous NaHCO3 solution
  2. extractionThe crude product was extracted with CH2Cl2
  3. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5-8% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-0b67dd7c717f4bd5ab54e6f613f87550
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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