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

HRID 1595069Notes

Reaction equation

HRID 1595069 reaction equation
BrCC[CH:4]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[CH3:19][CH2:20][O-].[Na+].[C:23]([OH:29])(=[O:28])[CH2:24][C:25]([OH:27])=[O:26].[CH2:30]([CH:32]([CH2:36][CH3:37])[C:33]([NH2:35])=[O:34])[CH3:31]>C(O)C.CN(C)C=O>[CH2:30]([CH:32]([CH2:36][CH3:37])[C:33]([NH2:35])=[O:34])[CH3:31].[C:23]([O:29][CH2:19][CH2:20][C:12]1[CH:11]=[CH:10][C:9]([C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:14][CH:13]=1)(=[O:28])[CH2:24][C:25]([O-:27])=[O:26]

Participants

6

Reactant 3

HCID 2723922Sodium ethoxide2×HCID 217075234-(2-Bromoethyl)octanophenoneHCID 22466969Diethyl acetamide malonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The fraction which contains 4-(2-bromoethyl)octanophenone prepared in the step N (500 mg) was dissolved in anhydrous ethanol (2 ml) to obtain a solution. Sodium ethylate (164 mg) was added to the solution. The mixture was stirred under atmosphere of nitrogen at 60° C. for 1 hour. The suspension was dissolved in N,N-dimethylformamide (10 ml) to obtain a solution. Diethyl acetamide malonate (1050 mg) and sodium ethylate (245 mg) were added to the solution, and 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 (1:0e3:1) as an eluate to obtain diethyl acetamide-2-(4-octanoyl phenyl)ethyl malonate (477 mg) in the form of colorless crystal.

Workup

  1. customprepared in the step N (500 mg)
  2. customto obtain a solution
  3. customto obtain a solution
  4. stirringthe solution was stirred under atmosphere of nitrogen at 60° C. overnight
  5. extractionextracted with ether
  6. washwashed with saturated saline solution
  7. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-355534a247e14e3b8226fd574da83dd5
Source dataset
uspto-grants-2001_09
Patent number
US06284915B1

Reaction notes

Loading…