Diethyl Malonate → HCID 86746211, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence