Cyclooctanone → HCID 56979075, compound

Participants

Reaction Conditions

Reaction Steps

Cyclooctanone Compound 1a (2.5 g, 19.8 mmol) in THF (5 mL) was added dropwise to a solution of LiHMDS (23.8 mL, 23.8 mmol) in anhydrous THF (50 mL) at −78° C. under a N2 atmosphere. The mixture was stirred at −78° C. for 60 mins, then 1-bromomethyl-3-chloro-benzene Compound 3a (4.1 g, 19.9 mmol) in anhydrous THF (10 mL) was added dropwise. The mixture was stirred for 5 hrs, while warming to r.t. The reaction was quenched with water (5 mL) and the organic layer was diluted with EtOAc (100 mL), then washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude oil which was purified by flash chromatography using 3% EtOAc in hexane to afford 2-(3-chloro-benzyl)-cyclooctanone Compound 3b (4.12 g, 82.6%).

Provenance & Evidence