N-bromobutanimide → Ethyl 2-bromo-2-(pyridin-4-yl)propanoate

HRID 46098ノート

反応式

HRID 46098 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>CC#N.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>[Br:14][C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

6

反応物 2

HCID 67184N-bromobutanimideHCID 11651240Ethyl 2-(pyridin-4-yl)propanoate

生成物 1

HCID 58930190Ethyl 2-bromo-2-(pyridin-4-yl)propanoate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒HCID 10340Sodium Carbonate溶媒

実験手順

The above compounds were prepared according to the procedure reported in the literature: see D. Yang, J. Org. Chem. 2002, 67, 7429. MS: 258, 260 (M+1). To a solution of ethyl 2-(pyridin-4-yl)propanoate (5.3 g, 30 mmol), Mg(ClO4)2 (Aldrich, 2.0 g, 9.0 mmol) in CH3CN (60 mL) was added N-bromosuccinimide (Aldrich, 5.9 g, 33 mmol) at room temperature. After 2 h, the reaction mixture was diluted with ether (200 mL), and 10% Na2CO3. The organic phase was separated, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. Mass Spec. m/z+ion 258, 260 (M+1).

後処理

  1. customThe above compounds were prepared
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-db7576fa46da4260a610fe041ea2cf0f
出典データセット
uspto-grants-2013_09
特許番号
US08541592B2

反応ノート

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