Trimethylsulfonium iodide → 3-(2-(7-Chloroquinolin-2-yl)cyclopropyl)anisole

Participants

Reaction Steps

To trimethylsulfonium iodide (9.98 g, 2. eg.) in 60 mL of THF was added, at -10° C., 15 mL of n-BuLi (1.6M in hexane). The temperature was raised to room temperature for 2 hours. Then, at -10° C., the alkene (from Step 1) (7.037 g, 23.8 mmoles) in 30 mL of THF was added. After 30 minutes at -10° C., the reaction mixture was stirred overnight at room temperature. Hydrolysis with 25% aqueous NH4OAc, extractions with ethyl acetate and flash chromatography with toluene yielded the desired product.

Provenance & Evidence