Diethyl Malonate → Diethyl 2-(7-octenyl)malonate

HRID 1267745Notes

Reaction equation

[H-].[Na+].O1CCCC1.[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27]>O>[CH2:27]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([O:16][CH2:17][CH3:18])=[O:15])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=[CH2:20]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60%, 6.3 g, 156.96 mmol) was added to anhydrous tetrahydrofuran (200 ml) under argon atmosphere and cooled to 0° C. To this mixture, diethyl malonate (23.8 ml, 156.95 mmol) was slowly added dropwise, followed by stirring for 1 hour at room temperature. After cooling to 0° C., 8-bromo-1-octene (20 g, 104.64 mmol) was slowly added to the reaction mixture, followed by stirring for 12 hours at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/30) to give diethyl 2-(7-octenyl)malonate (16 g, Yield 56.56%) as a colorless oil.

Workup

temperatureAfter cooling to 0° C.
stirringby stirring for 12 hours at room temperature
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/30)

Sources & evidence

ORD record: ord-fc1cb4e2bbc24cef956f9945ea3983da
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552068B1

Reaction notes

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