Phenethyl bromide → Diethyl acetamido(2-phenylethyl)propanedioate

HRID 1795701Notes

Reaction equation

HRID 1795701 reaction equation
[H-].[Na+].[C:3]([NH:6][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4].[C:18]1([CH2:24][CH2:25]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[C:3]([NH:6][C:7]([CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydride

Product 1

HCID 227959Diethyl acetamido(2-phenylethyl)propanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (50.6 g) in dimethylformamide (1500 ml) was dropwise added a solution of diethyl acetamidomalonate (250 g) in dimethylforamide (200 ml) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. 2-Phenylethyl bromide (156 ml) was dropwise added thereto and the resultant mixture was stirred for 7 hours at room temperature. The reaction mixture was poured into ice water (1500 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled away. The obtained residue was crystallized from toluene to give the title compound (102 g) as white crystals, melting point 115-117° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away
  6. customThe obtained residue was crystallized from toluene

Sources & evidence

ORD record
ord-d7b0d6716b5e45659ee12c28fa8c18c2
Source dataset
uspto-grants-2006_04
Patent number
USRE039072E1

Reaction notes

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