Trimethoxysilane → 1-Nitro-2-[[[6-(trimethoxysilyl)hexyl]oxy]methyl]benzene

HRID 2216233Notes

Reaction equation

[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])([O-:3])=[O:2].[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])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C:5]1[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

Conditions

Temperature: 37 °C

Procedure

A 20-ml eggplant type flask was purged with nitrogen, and charged with 2.5 g (10.7 mmol) of 5-hexenyl 2-nitrobenzyl ether, 1.56 g (12.8 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. After the temperature was returned to room temperature, the reaction mixture was purified by vacuum distillation using a short path. From the second fraction (0.2 mmHg/123–125° C.), 1.98 g of the desired product was obtained in a 52% yield.

Workup

customA 20-ml eggplant type flask was purged with nitrogen
temperatureThereafter, the bath temperature was raised to 100° C.
waitthe reaction was completed in 2 hours
customwas returned to room temperature
distillationthe reaction mixture was purified by vacuum distillation

Sources & evidence

ORD record: ord-2d9155c759fb4b829b13bde5566b9088
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112397B2

Reaction notes

Loading…