HCID 12507349, compound → HCID 10154049, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.1 g (1R,6S)-8,8-dichlorobicyclo [4.2.0]oct-2-en-7-one, prepared as shown in Example 3A, in 10 ml of glacial acetic acid was added 2.0 g of zinc dust in portions over a period of 15 minutes. The mixture was then stirred at 65° C. for 1 hour, then a further 0.5 g of zinc dust was added and the mixture stirred at 75° C. for 1 hour. The mixture was cooled, filtered, the solid washed with hexane, the filtrate and combined washings diluted with water and extracted with hexane. The hexane layer was dried over anhydrous sodium sulfate, the solvent removed under reduced pressure and the residue distilled under vacuum to give 500 mg of (1R,6S)-bicyclo[4.2.0]oct-2-en-7-one, the compound of formula (2), [α]D =+171.4°, (C=0.5, CHCl3).

Provenance & Evidence