Diethyl Malonate → HCID 18621549, compound

HRID 1861782Notes

Reaction equation

HRID 1861782 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[CH2:16]([C:23]1[CH:28]=[CH:27][N:26]=[C:25]([CH2:29]Cl)[CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCO>[CH2:16]([C:23]1[CH:28]=[CH:27][N:26]=[C:25]([CH2:29][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 18621444HCID 18621444, compound

Product 1

HCID 18621549HCID 18621549, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (1.15 mL, 7.60 mmol) was added to a solution of sodium ethoxide (0.106 g of sodium in 5.0 mL of EtOH). To the clear solution was then added gradually a solution of 4-benzyl-2-(chloromethyl) pyridine (0.59 g, 2.7 mmol) in EtOH (5 mL). After the mixture had been heated at reflux for 4.5 h, the EtOH was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL), washed with NH4Cl (2×50 mL)), dried over Na2SO4 and was concentrated under reduced pressure. The crude compound was purified by filtration on silica gel using EtOAc/n-hexane as eluant to afford the title compound as a colorless oil (0.9 g, 98%) 1H NMR (CDCl3) δ1.12 (t, J=7.2 Hz, 4H), 1.28 (t, J=7.2 Hz, 2H), 3.25-3.40 (m, 2H), 3.92 (s, 2H), 4.00-4.30 (m, 5H), 6.93 (d, J=4.8 Hz, 1H), 7.00 (s, -H), 7.15 (d, J=7.2 Hz, 2H), 7.20-7.40 (m, 3H), 8.38 (d, J=5.1 Hz, 1H); IR (film) 2984, 1752, 1736, 1606 cm−1.

Workup

  1. temperatureAfter the mixture had been heated
  2. temperatureat reflux for 4.5 h
  3. customthe EtOH was removed under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (50 mL)
  5. washwashed with NH4Cl (2×50 mL)),
  6. dry with materialdried over Na2SO4
  7. concentrationwas concentrated under reduced pressure
  8. filtrationThe crude compound was purified by filtration on silica gel

Sources & evidence

ORD record
ord-d6eaa952e9124bdcba18b7b2b6e9e0cb
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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