Trimethoxysilane → 4,5-Methylenedioxy-2-nitrobenzyl 3-(trimethoxysilyl)propyl ether

HRID 2216235

Reaktionsgleichung

[CH2:1]1[O:14][C:13]2[CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:5]([CH2:6][O:7][CH2:8][CH:9]=[CH2:10])=[CH:4][C:3]=2[O:2]1.[CH3:18][O:19][SiH:20]([O:23][CH3:24])[O:21][CH3:22]>[H+].[H+].O.O.O.O.O.O.Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH3:18][O:19][Si:20]([O:23][CH3:24])([O:21][CH3:22])[CH2:10][CH2:9][CH2:8][O:7][CH2:6][C:5]1[CH:4]=[C:3]2[O:2][CH2:1][O:14][C:13]2=[CH:12][C:11]=1[N+:15]([O-:17])=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 37 °C

Versuchsvorschrift

A 10-ml eggplant type flask was purged with nitrogen, and charged with 1.0 g (4.2 mmol) of allyl 3,4-methylenedioxy-6-nitrobenzyl ether, 0.616 g (5 mmol) of trimethoxysilane, and an infinitesimal amount of hydrogen hexachloroplatinate(IV) hexahydrate (H2PtCl6·6H2O), followed by stirring at 37° C. for 30 minutes. Thereafter, the bath temperature was raised to 100° C., and the reaction was completed in 2 hours. The reaction mixture was purified by silica gel column chromatography using a medium-pressure column. Using a mixture of hexane, ethyl acetate and tetramethoxysilane (in a volume ratio of 100:20: 1) as the eluent, 0.80 g (2.2 mmol) of the desired product was obtained in a 52% yield. Its Rf value (for the aforesaid eluent) was 0.1.

Aufarbeitung

customA 10-ml eggplant type flask was purged with nitrogen
temperatureThereafter, the bath temperature was raised to 100° C.
waitthe reaction was completed in 2 hours
customThe reaction mixture was purified by silica gel column chromatography
additiona mixture of hexane, ethyl acetate and tetramethoxysilane (in a volume ratio of 100:20: 1) as the eluent

Quellen und Nachweise

ORD-Eintrag: ord-8b6f05fc079d4e6cba0e3779d2c364df
Quelldatensatz: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07112397B2

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