Diethyl Malonate → Diethyl 2-(3-methyl-4-nitrophenyl)malonate

HRID 2114161Notes

Reaction equation

[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH3:24])[CH:16]=1>CN(C)C=O>[CH3:24][C:17]1[CH:16]=[C:15]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH:20]=[CH:19][C:18]=1[N+:21]([O-:23])=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (60% in mineral oil; 0.599 g) was suspended in dimethylformamide (10 mL), and to this was added dropwise a solution of diethyl malonate (2.00 g) in dimethylformamide (10 mL) under ice-cooling. After the foam generation was finished, a solution of 4-fluoro-2-methylnitrobenzene (1.94 g) in dimethylformamide (5 mL) was added thereto. The reaction temperature was raised to 100° C., the mixture was stirred for 6 hours. The resulting reaction mixture was concentrated, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over sodium sulfate, concentrated, and purified by column chromatography on silica gel (ethyl acetate:hexane=1:5) to give the title compound (1.65 g) as a yellow oil.

Workup

temperaturecooling
customThe resulting reaction mixture
concentrationwas concentrated
extractionextracted with ethyl acetate
washThe extract was washed successively with water and saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated
custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record: ord-16cac0b87fcf44fab50ead357fd552b7
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432392B2

Reaction notes

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