Sodium hydride → HCID 53792436, compound

Participants

Reaction Steps

To a solution of the crude reaction product of the previous step, viz. about 5 g of 4-di(2-acetoxyethyl)amino cinnamaldehyde in 125 ml of dimethyl formamide (DMF) were added 6 g of diethyl-4-nitro-benzyl phosphonate, prepared as prescribed by D. H. Wadsworth et al. in the Journal of Organic Chemistry, Vol. 30 (1965), p. 680 ff and, in small successive portions, 1.2 g of sodium hydride in the form of a 60%-dispersion in mineral oil, supplied by Jansses Chimica of Beerse, Belgium. The reaction mixture was stirred for 1 hour at room temperature and then poured, with vigorous stirring at 0° C., into a mixture of 400 ml of dichloromethane, 200 ml of water, and 20 ml of acetic acid. The organic layer was separated, washed twice with a saturated solution of sodium chloride, dried on magnesium sulphate, and concentrated by evaporation to a small volume. The residue was dissolved in 125 ml of dimethyl formamide (DMF), to which was added a solution of 8 g of sodium hydroxide in 25 ml of water. The resulting clear solution was boiled for 30 minutes with refluxing and then poured, with vigorous stirring, into 500 ml of water. The resulting precipitate was filtered off and after-washed with water until the filtrate had a pH of 7. The crude product after drying was crystallized from a mixture of 25 ml of dimethyl formamide (DMF) and 75 ml of dichloromethane. Obtained were 4.0 g of pure 1-(4-di-hydroxyethyl)aminophenyl)-4-(4-nitrophenyl)-1,3 butadiene having a melting point of 195°-198° C.

Provenance & Evidence