Methyl iodide → 1-o-Oleyl-2-o-methyl-3-o-trityl glycerol

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Reaction Steps

Diol Compound 20 (2.0 g, 5.97 mmol) was added dropwise to a solution of trityl chloride (1.66 g, 6.0 mmol) in anhdyrous pyridine (10 mL). The reaction was left to stir for 16 hours after which the solvent was removed by co-evaporation with toluene (2×5 mL). Then, part of the residue (1.0 g, 1.7 mmol) was added dropwise to a suspension of NaH (0.14 g, 3.4 mmol) in THF (50 mL), followed by the addition of MeI (0.22 mL, 3.4 mmol). After 16 hours, TLC analysis showed that the reaction had gone to completion and H2O (5 mL) was added followed by concentration of the reaction mixture. The residue was partitioned between H2O (20 mL) and diethyl ether (100 mL), the organic extract was washed with sat. NaHCO3 (10 mL), dried (MgSO4) and concentrated to give 1-O-oleyl-2-O-methyl-3-O-trityl glycerol (Compound 21) as an oil. Crude Compound 21 (1.16 g) was dissolved in CH2Cl2 (10 mL) after which trifluoroacetic acid (2 mL) was added. The reaction mixture was stirred for 5 min and excess TFA was quenched by adding solid NaHCO3 until effervescence ceased. The mixture was diluted with H2O (10 mL), extracted with CH2Cl2 (2×50 mL) and the combined organic phases were dried (MgSO4), concentrated and subjected to silica-gel column chromatography [eluent: hexane/ethyl acetate, 80/20, v/v] to give glycerol derivative Compound 22 (0.28 g, 42%) as an oil.

Provenance & Evidence