Methyl acetoacetate → HCID 14459258, compound

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Reaction Steps

0.59 ml (5.4 mmol) of methyl acetoacetate is added dropwise under nitrogen to a suspension of 135 mg (5.6 mmol) of sodium hydride in 14 ml of tetrahydrofuran at -5° C. After 15 minutes, 4.0 ml (5.6 mmol) of 15% strength n-butyllithium in n-hexane are added dropwise at -5° C. the mixture is stirred for 15 minutes, a solution of 1.3 g (5.9 mmol) of zinc bromide in 20 ml of THF is added, the mixture is stirred for 15 minutes and a solution of 0.6 g (1.8 mmol) of the compound from Example 5 in 6 ml of tetrahydrofuran is added. After 30 minutes at -5° C., the mixture is hydrolyzed using saturated ammonium chloride solution, washed three times with dichloromethane, and the organic phase is dried and 380 mg are obtained after removing the solvent and washing the residue with petroleum ether.

Provenance & Evidence