Butylamine → (1E,6E)-1,7-bis[4-(2-morpholinoethoxy)phenyl]hepta-1,6-diene-3,5-dione

Participants

Reaction Conditions

Reaction Steps

To 2.0 g of pentane-2,4-dione were added 10.0 mL of AcOEt and 0.70 g of boron oxide, and the mixture was stirred at 70° C. for 1 hour. To the reaction mixture, 30 mL of a solution of 9.4 g of 4-(2-morpholinoethoxy)benzaldehyde in AcOEt and 10.7 mL of tributyl borate were successively added, and the mixture was stirred at the same temperature for 1 hour. To this, 0.4 mL of 1-butylamine was added, and the mixture was stirred at 70° C. for 2.5 hours and was allowed to cool back to room temperature. To the reaction mixture, 50 mL of a 10% K2CO3 aqueous solution and 30 mL of THF were added, and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated, washed with saturated brine, dried over MgSO4, and concentrated. The residue was treated with 100 mL of diethyl ether to give 2.51 g of the title compound as a powder (24% yield).

Provenance & Evidence