Water → Diethyl 2-(6-heptenyl)malonate

HRID 1267751Notes

Reaction equation

[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].O>O1CCCC1>[CH2:21]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60%, 5.78 g, 144.59 mmol) was added to anhydrous tetrahydrofuran (250 ml) and cooled to 0° C. To this mixture, diethyl malonate (25.09 g, 156.64 mmol) was slowly added dropwise, followed by stirring for 1 hour at room temperature. 7-Iodo-1-heptene (27 g, 120.49 mmol) dissolved in anhydrous tetrahydrofuran (50 ml) was then slowly added dropwise to the mixture, followed by stirring for 12 hours at room temperature. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40) to give diethyl 2-(6-heptenyl)malonate (25.8 g, Yield 84%).

Workup

additionwas then slowly added dropwise to the mixture
stirringby stirring for 12 hours at room temperature
extractionwas then extracted twice with ethyl acetate
washThe combined organic layers were washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40)

Sources & evidence

ORD record: ord-4e6a7302a653429c8cb588779f798d95
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552068B1

Reaction notes

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