Pyridine → HCID 86743950, compound

Participants

Reaction Steps

To a solution of 2-methoxy-5-hydroxymethyldibenzo[a,d]cycloheptene (10.5 g) in dry dichloromethane (150 ml) was added p-toluenesulphonyl chloride (8.1 g), pyridine (6.6 g) and 4-dimethylamino pyridine (300 mg). The reaction mixture was refluxed for 15h, cooled, washed with water (2×200 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica chromatography using 15% ethyl acetate in hexane as eluent to give the title compound as an oil (13.5 g). δ(360 MHz, CDCl3), 2.44 (3H, s, Ar--CH3), 3.78 (3H, s, OCH3), 4.19-4.31 (3H, m CH-CH2 --OSO2Ar). 6.58 (1H, d, J=11.9 Hz, Ar--CH=CH--Ar), 6.65 (1H, d, J=11.9 Hz, Ar--CH=CH--Ar), 6.68 (1H, d, J=2.7, CH=C(OCH3)--CH), 6.85 (1H, dd, J=8.4 and 2.7 Hz, CH=C(OCH3)--CH) and 7.16-7.42 (9H, m, aromatics). m/e 406 (M+).

Provenance & Evidence