Water → Diethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-propylmalonate

HRID 617583Notes

Reaction equation

HRID 617583 reaction equation
[H-].[Na+].[CH2:3]([CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH3:5].[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][CH2:32]I)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][CH2:32][C:6]([CH2:3][CH2:4][CH3:5])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 16552Diethyl propylmalonateHCID 24758Sodium hydrideHCID 226187172-(2-Benzyloxyphenyl)ethyl iodide

Product 1

HCID 22618813Diethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-propylmalonateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (1.3 g) in dimethylformamide (15 ml), a solution of diethyl propylmalonate (6.6 g) in dimethylformamide (45 ml) was added under ice-cooling and the mixture was stirred at room temperature for an hour. To the solution was added a solution of 2-(2-benzyloxyphenyl)ethyl iodide (10 g) in dimethylformamide (30 ml), the mixture was stirred at the same temperature for an hour and left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and a saturated brine and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (10 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for an hour
  3. waitleft
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  6. dry with materiala saturated brine and dried over magnesium sulfate
  7. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-ceb0821ad4bf474e85df4fd486f764f5
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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