Reaction #543539

Reaction equation

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

cesium carbonate

benzylbromide

→

benzyl ester

Yield 82.2%

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

Yield 82.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   FiltrationInorganic salts were filtered
2. 2
   Washthe salts washed with acetonitrile
3. 3
   Otherevaporated
4. 4
   Otherto obtain an oil
5. 5
   OtherPurification by chromatography over silica gel (hexane: ethyl acetate, 7:3)

Procedure

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.

Source