Tert-Butanesulfinamide → (NE)-N-[(E)-4,4-dimethylpent-2-enylidene]-2-methylpropane-2-sulfinamide

HRID 12600

Reaktionsgleichung

Reaktionsgleichung von HRID 12600
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH3:8][C:9]([CH3:15])([CH3:14])/[CH:10]=[CH:11]/[CH:12]=O>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:8][C:9]([CH3:15])([CH3:14])/[CH:10]=[CH:11]/[CH:12]=[N:7]/[S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6]

Komponenten

5

Edukt 2

HCID 3382465Tert-ButanesulfinamideHCID 5362894Npc99789

Produkt 1

HCID 58986294(NE)-N-[(E)-4,4-dimethylpent-2-enylidene]-2-methylpropane-2-sulfinamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-methylpropane-2-sulfinamide (3.08 g, 0.025 mol) in dichloromethane (10 ml) was added CuSO4 (5.42 g, 0.034 mol) followed by (2E)-4,4-dimethylpent-2-enal (Journal of Organic Chemistry 1993, 58(9), 2517-22, 1.9 g, 0.017 mol) in dichloromethane (60 ml). The reaction mixture was stirred at RT overnight under nitrogen and then filtered through a pad of celite. The filtrate was evaporated under reduced pressure and purified by chromatography on silica gel eluting with 10% AcOEt/Hexane to give 2.1 g (58%) of the title compound; 1H NMR δ (ppm)(CDCl3, 400 MHz): 8.19 (1 H, d, J=9.2 Hz), 6.53 (1 H, d, J=15.7 Hz), 6.36 (1 H, dd, J=9.2, 15.7 Hz), 1.21 (9 H, s), 1.12 (9 H, s).

Aufarbeitung

  1. filtrationfiltered through a pad of celite
  2. customThe filtrate was evaporated under reduced pressure
  3. custompurified by chromatography on silica gel eluting with 10% AcOEt/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-eaef31384a664eadb0c135127658cd34
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728022B2

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