Acetamidomalonic acid diethyl ester → Diethyl 2-acetamido-2-(diphenylmethyl)malonate

HRID 35154

Reaction equation

HRID 35154 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[C:17]1([CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:2]([NH:5][C:6]([CH:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 236603BromodiphenylmethaneHCID 5360545Sodium

Product 1

HCID 14211495Diethyl 2-acetamido-2-(diphenylmethyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve sodium (2 g) in 400 ml ethanol and add diethyl acetamidomalonate (10.4 g). Stir 5 minutes, add diphenyl bromomethane (12.4 g), and stir 7 hours at room temperature. Acidify the reaction mixture, partition between water and methylene chloride (CH2Cl2), dry the organic layer over magnesium sulfate (MgSO4), filter, and evaporate the solvent to obtain the crude title compound as a pale yellow oil. Rf (silica gel; Et2O)=0.89.

Workup

  1. stirringstir 7 hours at room temperature
  2. custompartition between water and methylene chloride (CH2Cl2)
  3. dry with materialdry the organic layer over magnesium sulfate (MgSO4)
  4. filtrationfilter
  5. customevaporate the solvent

Sources & evidence

ORD record
ord-18b2b873df424d9bacf447d4ae203cba
Source dataset
uspto-grants-1988_08
Patent number
US04766109

Linked notes

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