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

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Reaktionsgleichung

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]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-95fd680a5e824d02ba4445f870a42e47
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08633313B2

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