Tetradecyltrimethylammonium → 2-(4-Chlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propane-1,2-diol

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To a stirred solution of p-chlorophenacyl-1H-1,2,4-triazole (10.3 g, 40 mmol) in 65 mL of toluene and 65 mL of 20% w/w NaOH at 60° C., add trimethylsulfoxonium iodide (8.84 g, 40 mmol) and cetrimide (0.39 g). Continue to stir the so-formed mixture at 60° C. for 1.5 h. Separate the toluene layer, add 20 mL of H2O to the aqueous layer and extract with two 100 mL portions of ethyl acetate (EtOAc). Combine both the toluene and EtOAc layers, dry oyer MgSO4, filter, and evaporate off the solvents. Add 100 mL of acetone, 6 mL of concentrated H2SO4, 20 mL of H2O, and reflux for 3 hr. Eyaporate the acetone at 45° C. under reduced pressure. Add 20 mL of sat. sodium bicarbonate and extract with two 100 mL portions of EtOAc. Wash the combined EtOAc layers with sat. brine, dry oyer MgSO 4, and evaporate the EtOAc to obtain a syrup. Chromatograph the syrup on 300 g of silica gel using 5% MeOH/CH2Cl2 as the eluent under flash chromatography conditions to obtain 3.63 g of the title product.

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