Diethyl Malonate → 1,3-Diethyl 2-(3-phenylpropyl)propanedioate

HRID 1003974Notes

Reaction equation

HRID 1003974 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[C:14]1([CH2:20][CH2:21][CH2:22]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([CH2:20][CH2:21][CH2:22][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydride

Product 1

HCID 106363121,3-Diethyl 2-(3-phenylpropyl)propanedioateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An ice-cold solution of diethyl malonate (5.81 ml, 40 mmol) in dimethylformamide (60 ml) was treated portionwise with sodium hydride (1.6 g, 40 mmol 60% dispersion in oil). After 0.25 h 3-phenylpropylbromide (6.71 ml, 44 mmol) was added and the reaction stirred overnight at room temperature. Work-up and chromatography as described in Example 37a) gave the title compound as a colourless oil (10.8 g, 97%);

Sources & evidence

ORD record
ord-7141a2fe38d74ee991f16fc45e05d18c
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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