Hydrochloric Acid → HCID 18947423, compound

Participants

Reaction Steps

50 ml of a dry tetrahydrofuran solution containing 1 g of 16-hydroxyhexadecanoic acid, 1.1 g of tert-butyldimethylsilyl chloride and 0.75 g of imidazole, was stirred at room temperature for 12 hours under an inert atmosphere of nitrogen gas. The solvent was distilled off under reduced pressure, and then 200 ml of ethyl acetate was added. The mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a syrup product. Then, 40 ml of diethyl ether, 30 ml of methanol and 30 ml of 1N hydrochloric acid were added thereto, and the mixture was stirred at room temperature for 15 minutes. The solvent was distilled off under reduced pressure, and then 200 ml of ethyl acetate was added. The mixture was washed once with 200 ml of a saturated sodium hydrogencarbonate aqueous solution and then washed twice with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a syrup product. This product was purified by silica gel column chromatography (ethyl acetate: hexane =1:1) to obtain 1.4 g of 16-tert-butyldimethylsilyloxyhexadecanoic acid.

Provenance & Evidence