Diethyl Malonate → Diethyl 2-(4-nitrophenyl)malonate

HRID 28619

Reaction equation

HRID 28619 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].Br[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>O1CCCC1>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 114661-Bromo-4-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 10869708Diethyl 2-(4-nitrophenyl)malonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl malonate (320 mg, 2 mmol) in tetrahydrofuran (15 ml) was added a solution of potassium tert-butoxide in tetrahydrofuran (1 M, 2.2 ml, 2.2 mmol). After stirring for 10 minutes, 4-bromonitrobenzene (404 mg, 2 mmol) was added. After stirring for 12 hours, the reaction was quenched by addition of saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide crude 2-(4-nitro-phenyl)-malonic acid diethyl ester.

Workup

  1. stirringAfter stirring for 12 hours
  2. customthe reaction was quenched by addition of saturated aqueous ammonium chloride solution (50 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a863cbbd91f4c5a82377896d5c25583
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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