Methyl morpholine oxide → N-(2-Oxopropyl)benzamide

HRID 915665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915665
[OH:1][CH:2]([CH3:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]=[C:2]([CH3:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 10910143N-(2-hydroxypropyl)benzamide

Produkt 1

HCID 569897N-(2-Oxopropyl)benzamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Prepare a solution of N-(2-hydroxypropyl)benzamide (8.22 g, 45.9 mmol) in methylene chloride (100 mL). Add N-methylmorpholine N-oxide (7.0 g, 60.0 mmol) followed by powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propylammonium perruthenate in one portion. Stir the mixture for 30 minutes and then warm to room temperature for 1 hour and filter through Celite®. Concentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate to afford 6.1 g of N-(2-oxopropyl)benzamide as a white solid. MS: m/e=178 (MH+)

Aufarbeitung

  1. temperaturewarm to room temperature for 1 hour
  2. filtrationfilter through Celite®
  3. concentrationConcentrate the filtrate and flash-chromatograph on silica gel eluting with 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9ebfa026cad1413e977caaa07a299728
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265246B2

Notizen zur Reaktion

Wird geladen…