Tert-Butanesulfinamide → (NE)-N-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-ylidene]-2-methylpropane-2-sulfinamide

HRID 1802121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802121
[Si:1]([O:8][CH2:9][C:10](=O)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.[Cl-].[Na+].O>[Si:1]([O:8][CH2:9]/[C:10](=[N:19]/[S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 3382465Tert-ButanesulfinamideHCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanone

Produkt 1

HCID 87388767(NE)-N-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-ylidene]-2-methylpropane-2-sulfinamideAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

1-(tert-butyldimethylsilyloxy)propan-2-one (188 mg, 1.0 mmol) and Ti(OEt)4 (0.52 mL, 2.5 mmol) were dissolved in THF (5 mL). Then 2-methylpropane -2-sulfinamide (121 mg, 1.0 mmol) was added to the mixture under nitrogen atmosphere. The mixture was heated to 70° C. for 2 h. The mixture was poured into brine and filtered through a plug of Celite. The organic layer was concentrated and purified by silica gel chromatography using PE/EA (5/1) to give product the title compound (190 mg, 65%). EDI-MS (M+1): 292. 1H NMR (300 MHz, CDCl3) δ 4.152 (s, 2H), 2.248 (s, 3H), 1.156 (s, 9H), 0.839 (s, 9H), 0.001 (s, 6H).

Aufarbeitung

  1. filtrationfiltered through a plug of Celite
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1505c45d2ade4cbf874a105cbbd7da47
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349849B2

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