Ammonium Chloride → 1-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one

HRID 1454964ノート

反応式

HRID 1454964 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[C:11][Si](C)(C)C)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[CH:11])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 575312291-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

生成物 1

HCID 575312331-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one収率 132%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-(6-chloropyridazin-3-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one (9.6 g, 26.4 mmol) in THF (200 mL) was added TBAF (32.9 mL, 32.9 mmol) at 0° C. After stirring at 0° C. for 15 min, the reaction was poured into aqueous NH4Cl, and extracted with EtOAc. The combined organic layers were washed with 1N HCl, brine, dried over MgSO4, and concentrated to an oil. The crude product was purified by silica gel chromatography (hexanes/CH2Cl2) to give title compound (10.2 g).

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with 1N HCl, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified by silica gel chromatography (hexanes/CH2Cl2)

出典と根拠

ORDレコード
ord-2569b45983884ea38e166400524385bf
出典データセット
uspto-grants-2009_01
特許番号
US07482345B2

反応ノート

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