Methyl acetoacetate → HCID 57219343, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% NaH (2.76 g, 69 mmol) in anhydrous DMF (50 mL) at 0° C. is added a solution of methyl acetoacetate (8 g) in DMF (50 mL) dropwise over 10 minutes. The mixture is cooled to -25° C. and 2.5M n-butyllithium (27.6 mL, 69 mmol) is added dropwise over 5 minutes. The mixture is stirred for 5 minutes and 1-bromo-3-phenylpropane (10.48 mL, 69 mmol) is added dropwise over 5 minutes. The cooling bath is removed and the mixture is stirred at room temperature for 2 hours. The mixture is poured into water and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (6:1 hexane:ethyl acetate) to produce methyl 3-keto-7-phenylheptenoate as an oil (8 g, 50% ): 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.50-1.68 (m, 4H), 2.42-2.62 (m, 4H), 3.40 (s, 2H), 3.70 (s, 3H), 7.10-7.18 (m, 2H), 7.18-7.30 (m, 3H).

Provenance & Evidence