Methyl morpholine oxide → 2,2-Diethyldihydro-2H-pyran-4(3H)-one

HRID 2167031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167031
[CH2:1]([C:3]1([CH2:10][CH3:11])[CH2:8][CH:7]([OH:9])[CH2:6][CH2:5][O:4]1)[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:10]([C:3]1([CH2:1][CH3:2])[CH2:8][C:7](=[O:9])[CH2:6][CH2:5][O:4]1)[CH3:11]

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 641051652,2-Diethyltetrahydro-2H-pyran-4-OL

Produkt 1

HCID 126596132,2-Diethyldihydro-2H-pyran-4(3H)-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of crude 2,2-diethyloxan-4-ol (500 mg, 3.2 mmol) in CH2Cl2 (10 ml) were added NMO (750 mg, 6.41 mmol) and 4 A molecular sieves (2 g). The solution was stirred for 30 mins and then TPAP (34 mg, 0.096 mmol) was added in one portion. The reaction was allowed to stir for 10 h. After checking the TLC, the alcohol was gone. It was filtered through a short pad of SiO2. The filtrate was concentrated and purified by normal phase SiO2 chromatography (0% to 50% EtOAc/hexanes) to give 2,2-diethyloxan-4-one (365 mg, 73%).

Aufarbeitung

  1. stirringto stir for 10 h
  2. filtrationIt was filtered through a short pad of SiO2
  3. concentrationThe filtrate was concentrated
  4. custompurified by normal phase SiO2 chromatography (0% to 50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b03e88120e714b14a2565a3b330bacde
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09044469B2

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