Sodium hydride → Methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

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Reaction Steps

To a round bottom flask containing methyl 2-(4-(4-bromophenyl)-4-(hydroxymethyl)cyclohexylidene)acetate (4.36 g, 12.85 mmol) was added 1,4-dioxane (161 ml). The clear solution was cooled in an ice-bath and sodium hydride (0.67 g, 16.75 mmol) was then added portion-wise. After the addition, the mixture was warmed to room temperature and stirred for 10 minutes. After 10 minutes of stirring, the content was heated to 100° C. in an oil bath (with a reflux condenser) for 30 minutes. The reaction mixture was cooled to room temperature and quenched with a saturated solution of ammonium chloride and subsequently concentrated to remove excess dioxane. The residue was taken in saturated ammonium chloride solution and extracted twice with EtOAc. The combined organic portion was dried over sodium sulfate and concentrated to afford a crude product. Column purification afforded the title compound as white solid (3.4 g, 78% yield). LC/MS, ESI-MS: 341.2 (M+H+), RT: 1.40 (Condition E).

Provenance & Evidence