Water → Dimethyl 2-(hept-6-en-1-yl)malonate

HRID 1268077Notes

Reaction equation

CC(C)([C:6]([O-:8])=[O:7])C([O-])=O.[H-].[Na+].I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].O.[CH3:21]CCCCC.[C:27]([O:30][CH2:31]C)(=[O:29])[CH3:28]>CS(C)=O>[CH2:13]([CH:28]([C:6]([O:8][CH3:21])=[O:7])[C:27]([O:30][CH3:31])=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Dimethylmalonate(8.16 ml, 71.4 mmol) was dissolved in anhydrous DMSO(60 ml), 60% sodium hydride(1.29 g, 53.55 mmol) was added thereto at 0° C., and the resulting mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added 7-iodohept-1-ene(8.0 g, 35.70 mmol), which was then stirred under heating at 60˜70° C. for 4 hours. The temperature was lowered to 0° C. and water was added. The mixture thus obtained was extracted with ethyl acetate, washed with water and saturated saline solution in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (eluent:n-hexane/ethyl acetate=40/1, v/v) to give 7.1 g(Yield 87.1%) of the pure title compound as a colorless oil.

Workup

stirringwas then stirred
temperatureunder heating at 60˜70° C. for 4 hours
customwas lowered to 0° C.
customThe mixture thus obtained
extractionwas extracted with ethyl acetate
washwashed with water and saturated saline solution in order
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (eluent

Sources & evidence

ORD record: ord-c98bc2a5d9ab443e8b100d74c22f1214
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555571B2

Reaction notes

Loading…