Reaktion #543539

Reaktionsgleichung

[3-(2-carboxyethyl)]-3-nitropentane-1,5-dicarboxylic acid

cesium carbonate

benzylbromide

→

benzyl ester

Ausbeute 82.2%

1,5-Bis(benzyloxycarbonyl)-3-[2-(benzyloxycarbony)ethyl]-3-nitro pentane

Ausbeute 82.2%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationInorganic salts were filtered
2. 2
   Waschenthe salts washed with acetonitrile
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto obtain an oil
5. 5
   SonstigePurification by chromatography over silica gel (hexane: ethyl acetate, 7:3)

Vorschrift

To a mixture of [3-(2-carboxyethyl)]-3-nitropentane-1,5-dicarboxylic acid (2.8 g, 0.01 mole) (prepared as described by James K. Young et al., Macromolecules, 1994, 27, 3464-34-71) and cesium carbonate (3.25 g, 0.025 mol) in acetonitrile (20.0 mL) was added benzylbromide (8.55 g, 6.0 mL, 0.05 mole) and the mixture stirred at RT for 24 h. Inorganic salts were filtered and the salts washed with acetonitrile. The filtrate and the washings were combined and evaporated to obtain an oil. Purification by chromatography over silica gel (hexane: ethyl acetate, 7:3) afforded the benzyl ester (40) as colorless viscous oil (4.5 g, yield: 82%). Mass Spectrum (M+H)hu +=548.

Quelle