Diethyl Malonate → HCID 53793296, compound

HRID 1856497Notes

Reaction equation

HRID 1856497 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[CH2:15][CH:16]=[C:17]([CH3:22])[CH2:18][N+:19]([O-:21])=[O:20]>O1CCCC1>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:15][CH:16]=[C:17]([CH3:22])[CH2:18][N+:19]([O-:21])=[O:20])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 544497411-Bromo-3-methyl-4-nitro-2-butene

Product 1

HCID 53793296HCID 53793296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.1 Mol of diethyl malonate and 0.25 Mol of sodium hydride in tetrahydrofuran was added a solution of 0.1 Mol 1-bromo-3-methyl-4-nitro-2-butene in tetrahydrofuran and stirred for 3 hours at room temperature. The reaction mixture was worked up via an acid extraction with ether. The excess of diethyl malonate was cautiously removed via distillation and the product purified by column chromatography over silica gel using ether/hexane 1:1 as eluent. A yellow oil was obtained.

Workup

  1. extractionThe reaction mixture was worked up via an acid extraction with ether
  2. customThe excess of diethyl malonate was cautiously removed via distillation
  3. customthe product purified by column chromatography over silica gel
  4. customA yellow oil was obtained

Sources & evidence

ORD record
ord-f03afc6b14784c70883d707f64a4defe
Source dataset
uspto-grants-1980_08
Patent number
US04219660

Reaction notes

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