Dichloromethane → HCID 136383550, compound

Participants

Reaction Steps

To a solution of 1 g (1.78 mmol) of 2-phenyl-10,12,15,16-tetrahydroxy-8-methoxy-11-methyl-9,14-dioxo-6,7,9,14-tetrahydronaphthaceno[1,2-g]phthalazin-1-one (5) in 10 m of CH2Cl2 are successively added, while stirring, at intervals of a few minutes 10 m of water, 10 mg of tetrabutylammonium bromide, 120 mg (3 mmol) of finely powdered sodium hydroxide and 0.26 m (2.8 mnmol) of allyl bromide. After 24 h at room temperature, the mixture is diluted with 40 m of water and acidifed with 10 per cent aqueous HCl. The organic phase is separated off, and the aqueous phase is extracted twice with 30 m of CH2Cl2. The combined organic phases are dried over MgSO4 and, without previous concentration, filtered through 20 g of silica gel 60, eluted with CH2Cl2 until colourless, and evaporated to dryness. 370 mg of the product are obtained. The yield is 35% of theory.

Provenance & Evidence