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

HRID 1595065Notes

Reaction equation

HRID 1595065 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[CH2:8]([CH:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12])[CH3:9].CC[O-].[Na+].I[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:25][CH:24]=1>C(O)C>[CH2:8]([CH:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12])[CH3:9].[C:1]([O:7][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:25][CH:24]=1)(=[O:6])[CH2:2][C:3]([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 111320764'-(2-Iodoethyl)octanophenoneHCID 22466969Diethyl acetamide malonate

Product 1

HCID 86757349Diethyl acetamide 2-(4-octanoyl phenyl)ethyl malonateYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4′-(2-Iodoethyl)octanophenone (175 g) prepared in the step D-3 was dissolved in anhydrous tetrahydrofuran (700 ml) to obtain 4′-(2-iodoethyl)octanophenone solution. Diethyl acetamide malonate (320 g) and sodium ethylate (100 g) was dissolved in anhydrous ethanol (1050 ml), and the 4′-(2-iodoethyl)octanophenone (175 g) solution was added, and the solution was heated to reflux for 7 hours. Tetrahydrofuran was removed by distillation from the solution. The solution was poured into ice water to obtain a precipitate which was recrystallized from hexane-ethyl acetate (40:1) to obtain diethyl acetamide-2-(4-octanoyl phenyl)ethyl malonate (110 g) in the form of colorless crystal.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 7 hours
  3. customTetrahydrofuran was removed by distillation from the solution
  4. additionThe solution was poured into ice water
  5. customto obtain a precipitate which
  6. customwas recrystallized from hexane-ethyl acetate (40:1)

Sources & evidence

ORD record
ord-6b4feb4e09164f97b8cc5bd710e71bda
Source dataset
uspto-grants-2001_09
Patent number
US06284915B1

Reaction notes

Loading…