Diethyl Malonate → Ethyl 2,9-diethoxycarbonylnonanoate

HRID 2268440Notes

Reaction equation

HRID 2268440 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[NH4+]>C(O)C>[CH2:10]([O:9][C:1]([CH:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 25517Ammonium ChlorideHCID 264813Ethyl 8-bromooctanoateHCID 2723922Sodium ethoxide

Product 1

HCID 18348648Ethyl 2,9-diethoxycarbonylnonanoateYield 67.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (9.85 g, 61.5 mmols) was added to an ethanol (170 ml) solution of sodium ethoxide (4.61 g, 67.7 mmols) with cooling with ice, and then stirred for 15 minutes at room temperature, and thereafter ethyl 8-bromooctanoate (17.0 g, 67.7 mmols) was added thereto. The reaction mixture was heated under reflux for 2 hours, and then an aqueous saturated ammonium chloride solution was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The thus-obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain the entitled compound (13.7 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated in vacuo
  8. customThe thus-obtained crude product
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-33d2b3341d964e5e945fa83036a9038e
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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