(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of triethylphosphonoacetate (10.7 g; 48 mmol) in tetrahydrofuran (5 ml) was added to a suspension of 60% sodium hydride dispersion (1.91 g; 48 mmol) in tetrahydrofuran (30 ml) maintaining the temperature between 5–15° C. A solution of bicyclo[3.2.0]hept-2-en-6-one (5 g; 46 mmol) in tetrahydrofuran (5 ml) was added maintaining the temperature between 5–15° C. The reaction mixture was stirred at ambient temperature for 30 minutes then demineralised water (30 ml) added. The phases are separated and toluene (20 ml) was added to the organic layer which was washed with demineralised water (2×20 ml). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a oil (7.74 g). maintaining the temperature between 5–15° C maintaining the temperature between 5–15° C added The phases are separated toluene (20 ml) was added to the organic layer which was washed with demineralised water (2×20 ml) The organic phase was dried over anhydrous magnesium sulfate filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1 N sodium hypochlorite in 0.1 N sodium hydroxide (478 ml) and 2 N sulphuric acid (425 ml) was added to a solution of bicyclo[3,2,0]hept-2-ene-6-one (23.0 g) in acetone (500 ml). The resulting solution was stirred at room temperature for 24 hours.