Cyclobutanone → HCID 90203880, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-4-chloropyridine (CAN 36953-42-1, 1 g, 5.2 mmol) in dry THF (25.0 ml) cooled down to −15° C. under an argon atmosphere was added isopropyl magnesium chloride, lithium chloride complex 1.3M solution in THF (4.2 ml, 5.46 mmol) and the reaction mixture was stirred at −15° C. for 1 hour. To the reaction mixture at −15° C. was slowly added cyclobutanone (CAN 1191-95-3, 401 mg, 428 μl, 5.72 mmol) and the reaction was stirred at −15° C. for 2 hours. The reaction was then let to warm up to 0° C. and stirred at 0° C. for 2 hours. Reaction was quenched by addition of water and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and extraction with an 3.0M aqueous solution of ammonium chloride. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (832 mg, 78%) as a yellow oil. MS (ESI, m/z): 184.3 (MH+).

Provenance & Evidence