5-Bromo-2-methyl-2-pentene → HCID 19043760, compound

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Reaction Steps

A solution of 6.3 g of N-methoxy-N-methyl-trimethylsilanyioxybenzamide is added dropwise at 0° C. to a Grignard reagent prepared from 1 g of magnesium and 5.7 g of 1-bromo-4-methyl-3-pentene. The reaction mixture is left to stand at room temperature overnight while stirring. The mixture is treated with 10% aqueous KHSO4 solution and then extracted with ethyl acetate. The organic phase is washed neutral with 10% aqueous NaCl solution, then dried and concentrated. The silyl group is cleaved in 10% aqueous THF with 1N hydrochloric acid. Then, the product is taken up in methylene chloride, dried and evaporated. After chromatography over silica gel while eluting with methylene chloride/5% methanol, there are obtained 2.1 g of 1-(4-hydroxy-phenyl)-5-methyl-hex-4-en-l-one. MS: m/e 204 (M+).

Provenance & Evidence