Hydrochloric Acid → HCID 59178687, compound

Participants

Reaction Steps

To a solution of 22.38 g of methyl acetate in 24.2 mL of toluene was added 11.66 g of sodium methoxide (28 wt % of methanol solution) at room temperature. To the obtained white suspension was added 5.00 g of 2-fluorobenzaldehyde at room temperature. After stirring at room temperature for 2 hours, methyl cyanoacetate and 7.77 g of sodium methoxide (28 wt % of a methanol solution) were further added thereto, followed by stirring at 65° C. overnight. The reaction mixture was cooled to room temperature, and 1 M hydrochloric acid (70 mL) and saturated brine were added thereto in this order, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 4.66 g of dimethyl 2-cyano-3-(2-fluorophenyl)pentanedioate as a pale yellow oily substance.

Provenance & Evidence