تفاعل #543539

ord-2f2846f132a549bb9a9af8356001e338

معادلة التفاعل

O=C(O)CCC(CCC(=O)O)(CCC(=O)O)[N+](=O)[O-]
[3-(2-carboxyethyl)]-3-nitropentane-1,5-dicarboxylic acid
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
BrCc1ccccc1
benzylbromide
O=C(CCC(CCC(=O)OCc1ccccc1)(CCC(=O)OCc1ccccc1)[N+](=O)[O-])OCc1ccccc1
benzyl ester
المردود 82.2%
O=C(CCC(CCC(=O)OCc1ccccc1)(CCC(=O)OCc1ccccc1)[N+](=O)[O-])OCc1ccccc1
1,5-Bis(benzyloxycarbonyl)-3-[2-(benzyloxycarbony)ethyl]-3-nitro pentane
المردود 82.2%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحInorganic salts were filtered
  2. 2
    غسيلthe salts washed with acetonitrile
  3. 3
    أخرىevaporated
  4. 4
    أخرىto obtain an oil
  5. 5
    أخرىPurification by chromatography over silica gel (hexane: ethyl acetate, 7:3)

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07186397B2uspto-grants-2007_03