Reaktion #55569

Reaktionsgleichung

tetranitromethane

ether

methyllithium

2-nitro-1-phenyl-1-propene

→

2,2-Dinitro-3-phenylbutane

Ausbeute 60.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGstirred an additional hour
4. 4
   SonstigeThe resulting product was isolated
5. 5
   Sonstigepurified
6. 6
   Sonstigeyielding 3.4 g (60% yield) of an analytically pure white crystalline product, mp 76°-78° C
7. 7
   SonstigeA similar procedure was used for the preparation of derivatives wherein R3 (see structure above or scheme)

Vorschrift

To a solution of 4.03 g (0.025 mol) of 2-nitro-1-phenyl-1-propene dissolved in 30 ml of dry THF (cooled to -40° C. with an acetronitrile-dry ice bath) and under a positive nitrogen atmosphere was added with stirring 22 ml (0.05 mol) of a 5% ether solution of methyllithium. The resulting solution was stirred for 1 h at -40° C. followed by the addition of 4.9 g (0.025 mol) of tetranitromethane. The solution was then allowed to warm to room temperature and stirred an additional hour. The resulting product was isolated and purified as described in Example 1 above, yielding 3.4 g (60% yield) of an analytically pure white crystalline product, mp 76°-78° C. A similar procedure was used for the preparation of derivatives wherein R3 (see structure above or scheme) was CH3 (CH2)3 and R2 was H and wherein R3 was CH3 and R2 was CH3 (see scheme).

Quelle