Benzyl Alcohol → HCID 58192798, compound

Participants

Reaction Steps

0.7 g of 4-Oxo-adamantane-1-carboxylic acid (11) were codistilled twice with toluene and dissolved in 5.5 mL of dry toluene. 1.1 mL of triethylamine were added. At 0° C., 0.9 mL of diphenylphosphoryl azide were added dropwise. The mixture was allowed to warm to room temperature and then the mixture was put into a preheated bath at 90° C. The mixture was heated until gas evolution ceased (ca. 1.5 h). 1.9 mL of benzyl alcohol were added and stirring was continued at 100° C. When the reaction was complete, it was cooled to room temperature, then ethyl acetate was added and the mixture was extracted twice with 1M aqueous sodium carbonate solution. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over sodium sulphate and evaporated. The resulting oil was subjected to silica gel chromatography (heptanes:ethyl acetate) to give 871 mg of the desired product. Rt=1.40 min (Method 3). Detected mass: 300.2 (M+H+).

Provenance & Evidence