Sodium hydride → 4-((2-Bromopyridin-3-yl)methyl)morpholin-3-one

HRID 1517602ノート

反応式

HRID 1517602 の反応式
[Br:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][C:13]1=[O:18]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:7]([CH2:8][N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 109010782-Bromo-3-(bromomethyl)pyridine

生成物 1

HCID 582686224-((2-Bromopyridin-3-yl)methyl)morpholin-3-one収率 66%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-bromo-3-bromomethyl-pyridine (0.68 g, 2.36 mmol) in dimethylformamide (10 mL) are added sodium hydride (0.11 g, 60% suspension, 2.82 mmol), morpholin-3-one (0.20 g, 1.97 mmol) and tetrabutylammonium iodide (catalytic) at 0° C. The mixture is stirred at room temperature for 16 hours. After completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL). The aqueous layer is extracted with ethyl acetate (2×25 mL) and the combined organic extracts are dried over sodium sulfate and concentrated in vacuo. The crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45) to yield 0.35 g (66%) of the title compound. MS (m/z): 271/273 (M+1, M+3).

後処理

  1. customAfter completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL)
  2. extractionThe aqueous layer is extracted with ethyl acetate (2×25 mL)
  3. dry with materialthe combined organic extracts are dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45)

出典と根拠

ORDレコード
ord-eca5ef5598b44329a6130dbd66720b76
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

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