Toluene → Diethyl 2-(4-benzyloxybenzyl)-2-(3-phenylpropyl)malonate

HRID 1871653Notes

Reaction equation

HRID 1871653 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.C1(C)C=CC=CC=1.[CH2:30]([O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Cl)=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CCCCCC.C(OCC)(=O)C.O.CN(C)C(=O)C>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]([CH2:42][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:44][CH:45]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 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 4

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

0.48 g of sodium hydride (55% oil suspension) was added to a mixture of 2.78 g of diethyl 2-(3-phenylpropyl)malonate, 20 ml of toluene and 10 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 30 minutes. Then, 2.45 g of 4-benzyloxybenzyl chloride was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes and then at 60° C. for 30 minutes. After the reaction, ethyl acetate and water were added to the reaction mixture, and then the ethyl acetate layer was separated. The extract thus obtained was dried over anhydrous magnesium sulfate and concentrated. The residue thus obtained was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 3.91 g of the desired compound as a syrup.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. waitat 60° C. for 30 minutes
  3. additionwere added to the reaction mixture
  4. customthe ethyl acetate layer was separated
  5. extractionThe extract thus
  6. customobtained
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-1fb63ae64b1e4453bb7587c08588b39b
Source dataset
uspto-grants-2000_08
Patent number
US06103907

Reaction notes

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