Methyl acetoacetate → HCID 17821749, compound

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Reaction Steps

0.5 ml (4.5 mmol) of methyl acetoacetate are added dropwise at 0° C.-5° C. under argon to a suspension of 0.15 g(5 mmol) of 80% pure sodium hydride in 6.5 ml of tetrahydrofuran p.a. After 15 minutes in each case, 3.65 ml (6 mmol) of 15% strength butyllithium in hexane are first added dropwise at 0° C. during the course of 10 minutes then a solution of 1.01 g (4.5 mmol) of dry zinc bromide in 4.5 ml of tetrahydrofuran and finally 0.51 g (1.5 mmol) of the compound from Example 123. The mixture is stirred overnight at room temperature, saturated ammonium chloride solution is added slowly, the aqueous phase is extracted using ethyl acetate, and the combined organic phases are washed using saturated sodium chloride solution, dried over sodium sulphate and concentrated. After column chromatography (φ3 cm) on 20 g of silica gel (230-400 mesh) using petroleum ether-ethyl acetate (1:1), 0.17 g (25% of theory) of yellowish oil is obtained. Rf =0.35 (petroleum ether-ethyl acetate (1:1)).

Provenance & Evidence