Diethyl Malonate → Ethyl 2-ethoxycarbonyl-9-phenoxynonanoate

HRID 610686Notes

Reaction equation

HRID 610686 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[CH2:11]([O:10][C:2]([CH:3]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 105162527-Phenoxyheptyl bromide

Product 1

HCID 18795066Ethyl 2-ethoxycarbonyl-9-phenoxynonanoateYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Sodium (0.22 g, 9.6 mmol) was dissolved in EtOH (20 mL). Diethyl malonate (1.53 g, 9.6 mmol) in EtOH (5 mL) and 7-phenoxyheptyl bromide (2.36 g, 8.7 mmol) in EtOH (5 mL) were subsequently added at room temperature. The reaction mixture was refluxed for 8 h. After evaporation of the solvent, the residue was taken up in ethyl acetate (150 ml). The organic phase was washed with water (2×50 mL), and brine (50 mL), and dried over Na2SO4. The crude product was purified by Kugelrohr distillation to give ethyl 2-ethoxycarbonyl-9-phenoxynonanoate (1.92 g, 63%), bp 150-154° C./0.1 torr, 1H-NMR: 1.24 (t, 6H), 1.1-1.8 (m, 12H), 3.30 (t, 1H), 3.91 (t, 2H), 4.18 (q, 4H), 6.7-7.2 (m, 5H).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. customAfter evaporation of the solvent
  3. washThe organic phase was washed with water (2×50 mL), and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. distillationThe crude product was purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-9d5194530c2b449796b30feeed9433fd
Source dataset
uspto-grants-1999_12
Patent number
US05998642

Reaction notes

Loading…