Dimethyl malonate → HCID 18626507, compound

HRID 368335Notes

Reaction equation

HRID 368335 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[CH3:20])[CH2:15]Br>CO>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[CH3:20])[CH2:15][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 7943Dimethyl malonateHCID 18509660122488-92-0

Product 1

HCID 18626507HCID 18626507, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.6 g (0.1124 g-atom) of Na in 50 mL of MeOH was treated with 12.9 mL (0.1124 mol) of dimethyl malonate and allowed to stir for 45 minutes. This was then treated dropwise with 24.17 g (0.1124 mol) of 3-methoxy-4-methylbenzyl bromide and the solution heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc. This was washed with 6% HCl, H2O, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave 28.54 g (95.5% yield) of the product as a pale yellow oil. The structure was confirmed by NMR spectroscopy.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washThis was washed with 6% HCl, H2O, saturated NaHCO3, and saturated NaCl
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ef320f77968a45e69988338a2c03cac8
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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