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Sodium ethoxide → Diethyl acetamide 2-(4-octanoyl phenyl)ethyl malonate

HRID 1595067
Notes
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Reaction equation

HRID 1595067 reaction equation
C1(C)C=CC(S([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)(=O)=O)=CC=1.[C:29](O)(=[O:34])[CH2:30][C:31]([OH:33])=[O:32].[CH2:36]([CH:38]([CH2:42][CH3:43])[C:39]([NH2:41])=[O:40])[CH3:37].CC[O-].[Na+]>C(O)C>[CH2:36]([CH:38]([CH2:42][CH3:43])[C:39]([NH2:41])=[O:40])[CH3:37].[C:29]([O:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:18]=1)(=[O:34])[CH2:30][C:31]([O-:33])=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 110477072-(4-Octanoyl phenyl)ethyl p-toluene sulfonateHCID 22466969Diethyl acetamide malonate

Product 1

HCID 86757349Diethyl acetamide 2-(4-octanoyl phenyl)ethyl malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-(4-Octanoyl phenyl)ethyl p-toluene sulfonate prepared in the step D-1 (500 mg), diethyl acetamide malonate (810 mg) and sodium ethylate (313 mg) were dissolved in anhydrous ethanol (1.5 ml)—anhydrous N,N-dimethylformamide (6 ml) to obtain a solution. The solution was stirred under atmosphere of nitrogen at 60° C. overnight. The reaction solution was poured into ice water, extracted with ether, and washed with saturated saline solution. The extracted solution was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography using hexane-ethyl acetate (1:0→3:1) as an eluate to obtain diethyl acetamide-2-(4-octanoyl phenyl)ethyl malonate (417 mg) in the form of colorless crystal.

Workup

  1. customto obtain a solution
  2. extractionextracted with ether
  3. washwashed with saturated saline solution
  4. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db37e0d601534b61a0ee22c4ffd2be56
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06284915B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes