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

HRID 473421노트

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HRID 473421 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
60 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-95fd680a5e824d02ba4445f870a42e47
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633313B2

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