Sodium hydride → Methyl 2-[(2'-cyano-2-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoate

HRID 519466ノート

反応式

HRID 519466 の反応式
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([F:30])[CH:17]=1>O1CCCC1>[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH:3]([C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])=[CH:17][C:18]=1[F:30])#[N:29]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 546075Methyl 3-oxoheptanoateHCID 670084324'-(Bromomethyl)-2'-fluorobiphenyl-2-carbonitrile

生成物 1

HCID 67009202Methyl 2-[(2'-cyano-2-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoate収率 108.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of methyl 3-oxoheptanoate (7 g) in tetrahydrofuran (30 mL) was added to a mixture of sodium hydride (1.2 g) and tetrahydrofuran (80 mL) at room temperature, and the mixture was stirred at room temperature for 30 min. And then, 4′-(bromomethyl)-2′-fluorobiphenyl-2-carbonitrile (5.3 g) was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated, the residue was extracted with 5% aqueous potassium hydrogensulfate solution and then with ethyl acetate, and the ethyl acetate layer was washed with saturated brine and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless oil (7.3 g, 90%).

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 3 days
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe residue was extracted with 5% aqueous potassium hydrogensulfate solution
  4. washwith ethyl acetate, and the ethyl acetate layer was washed with saturated brine
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-cce471d4e7dc41299034b62e2bcf0665
出典データセット
uspto-grants-2015_08
特許番号
US09115136B2

反応ノート

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