Water → Ethyl 2-(bicyclo[3.2.1]octan-3-ylidene)acetate

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (1.55 g, 38.7 mmol, 60% dispersion in oil) in 1,2-dimethoxy ethane (70 mL) at 0° C., triethyl phosphono acetate (8.38 mL, 41.9 mmol) was added. The resulting mixture was stirred 15 minutes at 0° C., 15 minutes at room temperature, and cooled to 0° C. Then, a solution of bicyclo[3.2.1]octan-3-one (Biogene, 4.0 g, 32.2 mmol) in 1,2-dimethoxy ethane (20 mL) was added and the resulting solution was stirred for 5 minutes at 0° C. and then stirred at room temperature overnight. Water was added and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with H2O (50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 25%) to give the title compound. MS (DCI/NH3) m/z 212 (M+NH4)+

Provenance & Evidence