Methyl vinyl ketone → HCID 14257057, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4,5-dichloro-6-methoxy-3-oxo-2-propylbenzofuran (0.785 g, 0.0029 mole) in tetrahydrofuran (THF) (8 ml) was warmed to 40° C. and treated with 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (10 μl) and then with methyl vinyl ketone (2 ml) over a 10 minute period. The reaction mixture was heated at 55° C. for 1/2 hour during which time DBN (2 x 10 μl) was added. The THF was evaporated in vacuo, the residual oil dissolved in ether and ethyl acetate, washed with water, dried over MgSO4 and evaporated in vacuo. The residual oil consisting of 4,5-dichloro-6-methoxy-3-oxo-2-(3-oxobutyl)-2-propylbenzofuran (0.81 g) was dissolved in ethanol (10 ml) and water (5 ml), treated with 5% NaOH (1 ml) and stirred at 25° C. for 72 hours. Treatment of the reaction mixture with water (5 ml) caused precipitation of 1,2-dichloro-3-methoxy-8-oxo-5a-propyl-5a,6,7,8,-tetrahydrodibenzofuran (0.6 g) which melted at 172°-173° C.

Provenance & Evidence