Methanol → Methyl 3-(2-(methylsulfonyl)phenyl)-3-oxopropanoate

HRID 473422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473422
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:15])[CH2:12][C:13]#N)(=[O:4])=[O:3].C[Si](Cl)(C)C.[OH2:21].[CH3:22][OH:23]>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:15])[CH2:12][C:13]([O:23][CH3:22])=[O:21])(=[O:4])=[O:3]

Komponenten

5

Edukt 4

HCID 887MethanolHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 126308083-(2-(Methylsulfonyl)phenyl)-3-oxopropanenitrile

Produkt 1

HCID 58318596Methyl 3-(2-(methylsulfonyl)phenyl)-3-oxopropanoate

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 3-(2-(methylsulfonyl)phenyl)-3-oxopropanenitrile (4.5 g, 20.25 mmol) in methanol (100 mL) was added trimethyl silyl chloride (11 mL, 100.58 mmol) at 25° C. The reaction mixture was stirred for overnight at 70° C. Water was added to the reaction mixture at 25° C. and extracted with EtOAc. The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel using 0-30% EtOAc in hexane to give methyl 3-(2-(methylsulfonyl)phenyl)-3-oxopropanoate: 1H NMR (400 MHz, DMSO-d6): δ 3.294 (S, 3H), 3.645 (s, 3H), 4.12 (s, 2H), 7.762-7.874 (m, 3H), 7.979-7.984 (m, 1H); LC-MS (ESI) m/z 256.9 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by column chromatography on silica gel using 0-30% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-d13ba1bf2d214cdbb61819132a80edfa
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633313B2

Notizen zur Reaktion

Wird geladen…