1,4-Dioxane → (2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone

HRID 526830ノート

反応式

HRID 526830 の反応式
O1CCOCC1.[Cl:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([Cl:24])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:25]([C:27]3[O:31][N:30]=[C:29]([CH3:32])[CH:28]=3)[OH:26])[CH:14]=2)[N:9]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([Cl:24])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:25]([C:27]3[O:31][N:30]=[C:29]([CH3:32])[CH:28]=3)=[O:26])[CH:14]=2)[N:9]=1

参加物

5

反応物 2

HCID 312751,4-DioxaneHCID 86716079(2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanol

生成物 1

HCID 86716078(2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

1,4-dioxane (7.5 mL) and manganese (IV) dioxide (447 mg, 5.14 mmol) were added to crude (2,4-dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanol (Intermediate 3: step a, 1.03 mmol assuming theoretical yield in prior step). The resulting black suspension was heated in a 100° C. oil bath in a sealed tube for 3 hours then cooled to room temperature. The mixture was then diluted with DCM, and filtered through Celite®. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 3-15% EtOAc-heptane) to afford slightly impure title compound which was used without further purification.

後処理

  1. customstep a, 1.03 mmol assuming theoretical yield in prior step)
  2. temperaturethen cooled to room temperature
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash column chromatography (silica gel, 3-15% EtOAc-heptane)

出典と根拠

ORDレコード
ord-82764dc173ce429faadb8966689d7532
出典データセット
uspto-grants-2016_05
特許番号
US09346782B2

反応ノート

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