Ethyl bromoacetate → 6-(4-carbethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.00 g (10.5 mmol) of the phenol prepared above, 1.60 g (11.6 mmol) of anhydrous K2CO3, 1.304 ml (11.8 mmol) of ethyl bromoacetate, and 40 ml of DMF is heated at 100° C. for 2 hrs under N2. The DMF is removed under vacuum and the residue taken up in 150 ml of EtOAc and 75 ml of water. The organic phase is washed with 50 ml of 5% aqueous NaOH, twice with saturated NaCl, dried (MgSO4), filtered, and the solvent removed to leave 2.186 g of a slightly yellow solid. This is recrystallized from hexane-EtOAc to give 2.01 g of 6-(4-carboethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone as a white, crystalline solid, m.p. 127°-129° C. Yield 69%.

Provenance & Evidence