Sodium Thiosulfate → 4-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanone

HRID 252046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252046
[CH3:1][C:2]1([CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]1.C[N+]1([O-])CCOCC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][C:2]1([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[O:3][CH2:4][C:5]([CH3:8])([CH3:9])[CH2:6][O:7]1

Komponenten

6

Edukt 3

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 231479574-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanol

Produkt 1

HCID 231479474-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanoneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

TPAP (161 mg, 0.05 eq.) was added to a solution of 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanol (2.22 g, 1 eq.) and NMO (2.28 g, 2 eq.) in MeCN (65 mL). The reaction mixture was stirred at room temperature overnight. Saturated aqueous solution of Na2S2O3 was added to the mixture and the resulting mixture was stirred vigorously for 15 minutes. The separated aqueous phase was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered through Celite and concentrated. The crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes) to give 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanone (1.87 g, 85%)

Aufarbeitung

  1. stirringthe resulting mixture was stirred vigorously for 15 minutes
  2. extractionThe separated aqueous phase was extracted with CH2Cl2
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered through Celite
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c847e169d6cd4642871842fcc15b9c0a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868002B2

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