Diiodomethane → HCID 24777030, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-chlorobenzoate (0.27 g, 1.58 mmol) and diiodomethane) in anhydrous tetrahydrofuran was added slowly to a vigorously stirred and heated (50° C.) slurry of samarium powder (1.0 g, 6.65 mmol) in tetrahydrofuran over 1.5 hours. After complete addition, the reaction mixture was stirred for 1 hour, than cooled (−10° C.), quenched with 1 N hydrochloric acid over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated. Purification by silica gel chromatography (1:1 hexanes in dichloromethane) afford 100 mg of 1-(3-chlorophenyl)cyclopropanol.

Provenance & Evidence