Pyridine → 2-Propanol, 1-(hexadecyloxy)-3-(triphenylmethoxy)-

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Reaction Steps

rac-1-O-Hexadecylglycerol (1.3 g, 4.17 mmol) and anhydrous pyridine (20 ml) were placed in a flame-dried 50 ml round-bottomed flask flushed with N2. Triphenylchloromethane (2.38 g, 8.54 mmol) was added to the solution and the reaction mixture was stirred for 48 hours. Ice cold H2O and ether were added. The ether layer was removed, washed with H2O, dried (MgSO4), and filtered. The solvent was removed under reduced pressure. Residual pyridine was removed as an azeotrope with toluene. The resulting white solid was dissolved in petroleum ether, and the solution refluxed for one hour to precipitate the triphenylmethanol. The solution was filtered and the petroleum ether removed to yield the crude product 36, rac-1-O-hexadecyl-3-O-tritylglycerol (2.73 g, theoretical yield=2.29 g ). The product was not purified further, but used directly in the next synthesis.

Provenance & Evidence