Phenethyl bromide → 1,3-Diethyl 2-(2-phenylethyl)propanedioate

HRID 1003971Notes

Reaction equation

HRID 1003971 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]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.C(OCC)C>[C:14]1([CH2:20][CH2:21][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

6

Reactant 3

HCID 7666Phenethyl bromideHCID 7761Diethyl MalonateHCID 24758Sodium hydride

Product 1

HCID 811191,3-Diethyl 2-(2-phenylethyl)propanedioateYield 71.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of diethyl malonate (6.07 ml, 40 mmol) in dimethyl formamide (60 ml) at 0° C. was treated portionwise with sodium hydride (1.6 g, 40 mmol, 60% dispersion in oil) and stirred for 0.25 h. 2-Phenylethyl bromide (5.48 ml, 40 mmol) in dimethylformarnmide (30 ml) was added dropwise. The mixture was warmed to room temperature and stirred for 1 h. The mixture was diluted with diethyl ether (300 ml), washed with water (4×200 ml), saturated brine (100 ml), dried (MgSO4) and evaporated. Flash chromatography on silica, eluting with 1% ethyl acetate in hexane, gave the title compound as a colourless oil (7.55 g, 71%); νmax (CH2Cl2), 1726 cm-1 ;

Workup

  1. stirringstirred for 1 h
  2. washwashed with water (4×200 ml), saturated brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. washFlash chromatography on silica, eluting with 1% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e8bc9da428ae4e9e98747ae9de0ed5e9
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

Loading…