Acetonitrile → Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 381152ノート

反応式

HRID 381152 の反応式
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17]C(CBr)=[C:15](C(C)C)[CH:14]=2)=[CH:7][CH:6]=1.[C:25]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=O)[CH3:26].[C:33]([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]#N>O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:25]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[C:26]([CH:40]([CH3:39])[CH3:33])[C:18]=2[CH3:17])=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 86585936Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate2 回

生成物 1

HCID 86585935Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate収率 58%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of methyl[4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate (Intermediate 156, 72.0 mg, 0.19 mmol) and 1-acetylimidazole (22.0 mg, 0.20 mmol) in 5 mL CH3CN was heated at 65° C. for 8 h and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (0.5% Et3N in 5% MeOH-EtOAc) afforded 40.0 mg (58%) of the title compound as a colorless solid.

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8a1347ceb07b4c639bd3b3caf55ade7e
出典データセット
uspto-grants-2001_10
特許番号
US06303785B1

反応ノート

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