4-Toluenesulfonyl chloride → 2,2-Dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile

HRID 11456

Reaktionsgleichung

C(N(CC)CC)C.[OH:8][CH:9]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[C:10]([CH3:14])([CH3:13])[C:11]#[N:12].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[CH3:13][C:10]([CH3:14])([CH:9]([C:15]1[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=1)[O:8][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])[C:11]#[N:12]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Triethylamine (1.57 ml, 11.3 mmol) was added to a solution of 3-hydroxy-2,2-dimethyl-3-(4-pyridyl)propionitrile (1.00 g, 5.67 mmol) in dichloromethane (20 ml) at room temperature. Further, p-toluenesulfonyl chloride (1.30 g, 6.80 mmol) was added to the mixture, and the whole was warmed at 50° C. with stirring for three days. The reaction mixture was allowed to stand and then concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 699 mg (37.4%) of 2,2-dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile as a pale yellow solid.

Aufarbeitung

concentrationconcentrated under reduced pressure
customthe concentrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e162f5a92b724cdcb52d12a66305c960
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07098226B2

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