Hydrogen Peroxide → 5-(Prop-2-en-1-yl)cyclopent-2-en-1-one

Participants

Reaction Steps

An ice cold (3° C.) solution of 2-phenylselenyl-5-(propene-3-yl)cyclopentanone, (mixture of isomers, (12.0 g, 43 mmol)) in methylene chloride (200 mL) was stirred in a 1 L round bottomed-flask that was equipped for boil-over containment. To this solution was added saturated aqueous ammonium chloride (45 mL), followed by dropwise addition of a 30% aqueous solution of hydrogen peroxide (22 mL). The reaction mixture was then slowly warmed to room temperature with intermittent cooling, as necessary, to prevent excess bubbling and boil-over. After stirring at room temperature for an additional hour the solution was washed with water (100 mL), followed by stirring with 10% aqueous sodium thiosulfate pentahydrate (75 mL) for 10 min, and the aqueous and organic layers were then allowed to separate. The organic solution was washed with saturated aqueous sodium bicarbonate and brine (75 mL each), dried using Na2SO4 and concentrated to a volume of about 30 mL. Purification of the crude reaction was effected by loading the crude mixture onto a silica gel column (˜400 cc) using methylene chloride as the eluting solvent. Concentration of the appropriate fractions afforded 5-(propene-3-yl)cyclopent-2-enone (3.95 g, 75%) as a very pale yellow oil. NMR (CDCl3): δ 7.61 (m, 1 H), 6.12 (m, 1 H), 5.60-5.75 (m, 1 H), 4.90-5.05 (m, 2 H), 2.70-2.80 (m, 1 H), 2.45-2.55 (m, 1 H), 2.30-2.40 (m, 2 H), 2.05-2.15 (m, 1 H).

Provenance & Evidence