Diethyl Ether → HCID 53982839, compound

Participants

Reaction Steps

To a solution of 3-bromo-5-hydroxy-dibenzo[a,e]cyclooctene (0.75 g) in dry dichloromethane (60 ml) was added pyridinium dichromate (2.1 g) and crushed 4 A molecular sieves (1.3 g). After stirring at room temperature for 14 h, diethyl ether (150 ml) Was added and the reaction mixture was filtered through a plug of celite. The solvent was removed and the residue purified by chromatography on flash silica with 5% ethyl acetate in hexane as eluent to give, as a colorless solid, the title compound (0.7 g). δ(360 MHz, CDCl3) 4.04 (2H, s, CH2 --C=O), 6.95 (1H, d, J=12.8 Hz, CHA =CHB), 7.09 (1H, d, J=12.8 Hz, CHA =CHB), 7.22-7.59 (6H, m, ArH), 8.36 (1H, d, J=2.2 Hz, C(O)--C=CH--CBr).

Provenance & Evidence