Benzyl Alcohol → HCID 86585468, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-diethyl 3-carboxy-3-methyl-5-(4-(octyl)phenyl)pentylphosphonate (0.165 g, 0.362 mmol) in tetrahydrofuran (1 ml) at 0° C. was added triethylamine (0.061 ml, 0.434 mmol) followed by methyl chloroformate (0.053 ml, 0.699 mmol). After stirring for 15 min, sodium azide (0.071 g, 1.08 mmol) in water (1 ml) was added. The ice bath was removed and the reaction stirred for 1 h. The reaction was diluted with ethyl acetate (25 ml) and washed with 2N aq HCl (25 ml), saturated aqueous sodium chloride (25 ml), dried over magnesium sulfate and concentrated to give a colorless oil. This oil was dissolved in toluene (1 ml), benzyl alcohol (0.056 ml, 0.543 mmol) was added and the solution heated to 90° C. for 4 h. The reaction was cooled, placed onto silica gel and eluted with hexane/acetone (70:30) to give a colorless oil (0.097 g): MS m/e 560.4 (M+).

Provenance & Evidence