Sodium hydride → HCID 19067911, compound

Participants

Reaction Steps

10.2 Grams of the mixture of 5-allyl-6-allyloxy-3,4-dihydro-2(1H)-quinolinone and 7-allyl-6-allyloxy-3,4-dihydro-2(1H)-quinolinone obtained in Example 16 was dissolved in 100 ml of dimethylformamide, then 2.2 g of 60% oily sodium hydride was added little by little, and stirred at 25° to 40° C. until generation of hydrogen gas was ceased. After the reaction mixture was cooled to room temperature, 9.1 g of prenyl bromide was added and stirred at room temperature for 8 hours. After the reaction was finished, water was added and extracted with methylene chloride, then the extract was washed with water and an aqueous solution saturated with sodium chloride in this order, and dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was concentrated. Thus obtained residual oily product was subjected to separation and purification by means of a silica gel flush column chromatography, there was obtained 10.2 g (59.7%) of 7-allyl-6-allyloxy-3,4-dihydro-1-prenyl-2(1H)-quinolinone.

Provenance & Evidence