Tetrahydrofuran → HCID 59457447, compound

Participants

Reaction Conditions

Reaction Steps

Compound 1b (7.0 g) was added to a solution of LHMDS (1M, 50 mL) in THF (50 mL) at −78° C. The mixture was stirred for 30 mins at −78° C. and then 1-bromomethyl-3-fluoro-benzene Compound 1c (8.80 g, 46.55 mmol) in THF (10 mL) was added dropwise. The mixture was stirred for 24 hrs while warming to room temperature. The reaction mixture was quenched with 1N HCl (5 mL), diluted with H2O (100 mL) and EtOAc (500 mL) and the organic layer was washed with brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude oil. Purification by flash chromatography (10% EtOAc in Hexane) to provide 2-(3-fluoro-benzyl)-cyclopentanone Compound 1d (5.20 g, 27.05 mmol, 58% yield) as a yellow oil.

Provenance & Evidence