Sodium ethoxide → Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoate

HRID 2268483Notes

Reaction equation

HRID 2268483 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([O-:9])=O.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>C(O)C.O>[CH2:2]([O:1][C:7]([CH:6]([CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)[C:5]([O:11][CH2:12][CH3:13])=[O:10])=[O:9])[CH3:3]

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 3595298Propanedioic acid, monoethyl esterHCID 18348598Ethyl 4-(3-iodopropoxy)benzoate

Product 1

HCID 18348516Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoateYield 47.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of sodium ethoxide (90%, 6.79 g) in ethanol (250 ml) was dropwise added ethyl malonate (12.0 g) with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 30 min and ethyl 4-(3-iodopropoxy)benzoate (25.0 g) was dropwise added with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) to yield the entitled compound (13.0 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. temperatureto warm to room temperature
  4. stirringstirred for 12 hr
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. customdried
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-cfa28ac0c36c4948a5eb142ec90c6d39
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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