Carbon tetrabromide → HCID 21186736, compound

Participants

Reaction Steps

In an atmosphere of argon, ethyl 9-hydroxymethyl-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (263.0 mg, 1.00 mmol) was dissolved in methylene chloride (5.0 ml), the solution was mixed with triphenylphosphine (393.0 mg, 1.50 mmol) at 0° C. and then with carbon tetrabromide (663.3 mg, 2.00 mmol) and the mixture was stirred at room temperature for 3 hours. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution and water and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine. After drying with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:5) to obtain the title compound (349.1 mg, quantitative) as white powder.

Provenance & Evidence