Acetic Acid → 6-(4-Fluorophenyl)-3-methylpyrazolo[5,1-b][1,3]oxazole

HRID 570131

反応式

HRID 570131 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH2:14][C:15]([CH3:17])=O)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]3[O:13][CH:14]=[C:15]([CH3:17])[N:10]3[N:9]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 178468630HCID 178468630、化合物

生成物 1

HCID 894883646-(4-Fluorophenyl)-3-methylpyrazolo[5,1-b][1,3]oxazole収率 46.3%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

To a stirred solution of 1-{[3-(4-fluorophenyl)-1H-pyrazol-5-yl]oxy}acetone (0.25 g, 1.0 mmol) in toluene, equipped with dean stark apparatus, acetic acid (2 ml) and p-TsOH (25 mg, cat.) was charged at RT and the reaction mass was refluxed at 130° C. for 16 h. After completion, the reaction was diluted with EtOAc (50 ml) and washed with brine. The organic layer dried over sodium sulphate and concentrated under reduced pressure to get the crude which was then purified by column chromatography 100-200 mesh) eluted with 5-10% ethyl acetate in hexane as eluent to get compound 6-(4-fluorophenyl)-3-methylpyrazolo[5,1-b][1,3]oxazole (0.1 g, yield 43%).

後処理

  1. additionwas charged at RT
  2. washwashed with brine
  3. dry with materialThe organic layer dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get the crude which
  6. customwas then purified by column chromatography 100-200 mesh)
  7. washeluted with 5-10% ethyl acetate in hexane as eluent

出典と根拠

ORDレコード
ord-3c0b78a0836c4cfebba1d3ef6e030625
出典データセット
uspto-grants-2015_05
特許番号
US09023844B2

関連ノート

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