Benzyl Alcohol → HCID 86598012, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.62 g (1.6 mmol) of (±)-diethyl 3-(carboxy)pentadecylphosphonate (from Example 27, Step B) in 5 mL of THF at 0° C. was treated with 0.27 mL (1.9 mmol) of TEA and 0.23 mL (1.9 mmol) of methyl chloroformate. The resulting mixture was stirred cold for 30 min, then treated with a solution of 0.51 g (7.9 mmol) of sodium azide in 3 mL of water. The resulting mixture was stirred for 2 h at 0° C. The reaction was diluted with 50 mL of EtOAc, washed with 50 mL of 2 N HCl, 50 mL of sat'd NaCl, dried and concentrated. The residue was dissolved in 5 mL of toluene, benzyl alcohol (0.33 mL, 3.2 mmol) was added and the solution was heated to 85° C. for 3 h. The reaction was cooled and directly purified by silica gel chromatography using 7:3 v/v hexane/acetone as the eluant to afford 0.45 g of the title compound: ESI-MS 498.3 (M+H).

Provenance & Evidence