Methanesulfonic Acid → 3-(2-(Methylsulfonyl)phenyl)-3-oxopropanenitrile

HRID 473421ノート

反応式

HRID 473421 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[CH2:9][C:10]#[N:11].[Na].[CH3:14][S:15](O)(=[O:17])=[O:16].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CS(C)=O.[Cu](I)I.O>[CH3:14][S:15]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[CH2:9][C:10]#[N:11])(=[O:17])=[O:16]

参加物

9

反応物 5

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 5360545SodiumHCID 107043343-(2-Bromophenyl)-3-oxopropanenitrile

生成物 1

HCID 126308083-(2-(Methylsulfonyl)phenyl)-3-oxopropanenitrile

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

To a solution of 3-(2-bromophenyl)-3-oxopropanenitrile (15 g, 66.94 mmol) in DMSO (267 mL) were added sodium salt of methanesulfonic acid (13.6 g, 138.89 mmol), copper iodide (6.3 g, 33.47 mmol), L-proline (3.8 g, 33.47 mmol) and sodium hydroxide (1.3 g, 33.47 mmol) at 25° C. The reaction mixture was stirred for 1 h at 60° C. Water was added to the reaction mixture at 25° C. and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 0-45% EtOAc in hexane to give 3-(2-(methylsulfonyl)phenyl)-3-oxopropanenitrile: 1H NMR (400 MHz, CHLOROFORM-d): δ 3.183 (S, 3H), 4.041 (s, 2H), 7.468 (dd, 1H, J=1.2 Hz, J=7.6 Hz), 7.699-7.798 (m, 2H), 8.084 (dd, 1H, J=1.2 Hz, J=7.6 Hz); LC-MS (ESI) m/z 224.0 [M+H]+.

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel using 0-45% EtOAc in hexane

出典と根拠

ORDレコード
ord-95fd680a5e824d02ba4445f870a42e47
出典データセット
uspto-grants-2014_01
特許番号
US08633313B2

反応ノート

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