Diethyl Malonate → HCID 86746211, compound

HRID 466639Notes

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].[CH3:14]/[C:15](/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20]I.[I-]>C1COCC1>[CH3:14]/[C:15](/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 192 mg (8.01 mmol) of NaH in 20 mL of THF at 0° C. under argon was added 1.21 mL (8.01 mmol) of diethyl malonate dropwise. The mixture was stirred at 0° C. for 0.5 hours at which time was treated with 1.0 g (2.67 mmol) of Example 4, Part A iodide in 2 mL of THF. After 1 hour at 0° C. the reaction was heated to 40° C. for 2 hours, then cooled to room temperature and stirred for 18 hours. The mixture was quenched with NH4Cl and diluted with ether. The organic layer was washed with H2O, brine, dried over MgSO4 and the solvent evaporated to provide 950 mg of a pale yellow oil. Flash chromatography was performed on 50 g of silica gel, packed, loaded and eluted with (95:5) hexane/ether. The pure product fractions were combined and evaporated to provide 580 mg (54%) of title compound as a pale yellow oil.

Workup

temperatureAfter 1 hour at 0° C. the reaction was heated to 40° C. for 2 hours
temperaturecooled to room temperature
stirringstirred for 18 hours
customThe mixture was quenched with NH4Cl
additiondiluted with ether
washThe organic layer was washed with H2O, brine
dry with materialdried over MgSO4
customthe solvent evaporated

Sources & evidence

ORD record: ord-983a9648d1e84480bbfedd02fef14018
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05157027

Reaction notes

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