Pyridine → HCID 86743949, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-hydroxymethyl-dibenzo [a,d]cycloheptene (6.1 g) in dry dichloromethane (60 ml) was added p-toluenesulphonyl chloride (4.9 g). pyridine (4 g) and 4-dimethylamino pyridine (100 mg). The reaction mixture was refluxed for 14 h, cooled, washed with water (2×50 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue. was purified by flash silica chromatography using 10% ethyl acetate in hexane as eluent to give the title compound as a colourless oil (8.2 g). δ (360 MHz, CDCl3) 2.46 (3H, s, CH3), 4.12 (1H, dd J=6.2 and 3.5 Hz, CH--CH2 --O), 4.24-4.32 (2H, m, CH--CH2 --O), 6.50 (1H, d, J=11.9 Hz, CHA =CHB), 6.73 (1H, d, J=11.9 Hz, CHA =CHB), 7.10-7.40 (11H, m, ArH).

Provenance & Evidence