Diethyl Malonate → Diethyl 2-pent-4-enylpropanedioate

HRID 1494086Notes

Reaction equation

HRID 1494086 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18]>C(O)C>[CH2:18]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:17][CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 707041-Pentene, 5-bromo-HCID 5360545Sodium

Product 1

HCID 361718Diethyl 2-pent-4-enylpropanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 300 mL of ethanol are added 5 g of sodium spheres and after a clear solution is obtained, 32.1 g of diethyl malonate is added in one portion. After 1 hour at room temperature, 15 g of 5-bromopent-1-ene is added and the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is evaporated to dryness and the residue is distilled under high vacuum to obtain diethyl pent-4-enylmalonate.

Workup

  1. customafter a clear solution is obtained
  2. customThe reaction mixture is evaporated to dryness
  3. distillationthe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-c794d2b781404eb9bf90b823205e2353
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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