Sodium hydride → Diethyl 2-(4-benzyloxybenzyl)-2-(3-phenylpropyl)malonate

HRID 1859943Notes

Reaction equation

HRID 1859943 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Cl)=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C(=O)C.C1(C)C=CC=CC=1>[CH2:23]([O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:35][C:12]([CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:37][CH:38]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 106363121,3-Diethyl 2-(3-phenylpropyl)propanedioate

Product 1

HCID 18625695Diethyl 2-(4-benzyloxybenzyl)-2-(3-phenylpropyl)malonateYield 82.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (55% suspension in oil, 0.48 g) was added to a solution of diethyl 2-(3-phenylpropyl)malonate (2.78 g) in a mixture of N,N-dimethylacetamide (10 ml) and toluene (20 ml). The mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture 4-benzyloxybenzyl chloride (2.45 g) was added and the mixture was stirred at ambient temperature for 30 minutes and then at 60° C. for 30 minutes. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and concentrated. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=9/1 as the eluant to afford the desired compound (3.91 g) as a syrup.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 30 minutes
  2. waitat 60° C. for 30 minutes
  3. customAt the end of this time the reaction mixture was partitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-989602d102074af5b0f175c6c799e1f4
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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