Diethyl Malonate → HCID 58778826, compound

HRID 1372558Notes

Reaction equation

HRID 1372558 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].[H][H].F[C:17]1[CH:18]=[CH:19][C:20]([N+:31]([O-:33])=[O:32])=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=1>CN(C=O)C.O>[CH2:24]([O:23][C:21]1[CH:22]=[C:17]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH:18]=[CH:19][C:20]=1[N+:31]([O-:33])=[O:32])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 58778826HCID 58778826, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In DMF (100 ml) was suspended sodium hydride (4.63 g, 115.7 mmol). Under cooling at 0° C. and stirring, diethyl malonate (18.5 g, 115.7 mmol) was added dropwise. After vigorous evolution of a hydrogen gas stopped, a solution of benzyl 5-fluoro-2-nitrophenyl ether (14.3 g, 57.8 mmol) in DMF (100 ml) was added to the reaction mixture at 0° C. The reaction mixture was stirred for 15 hours at room temperature. Water (500 ml) was poured and the mixture was extracted with ethyl acetate (300 ml). The extract was washed with saturated brine (200 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (3:1) eluate fractions, the title compound (22.0 g, 100%) was obtained as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for 15 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate (300 ml)
  3. washThe extract was washed with saturated brine (200 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (3:1) eluate fractions

Sources & evidence

ORD record
ord-9c940e15a9d448a3bcc0f4ddf9fa801a
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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