ethyl (3S)-3-hydroxytetradecanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (S)-3-hydroxytetradecanoate (2.00 g, 7.3 mmol) and 2-(chloromethyl)-3,5-dioxahexa-1-ene (manufactured by Tokyo Kasei Co., Ltd., 1.20 g, 8.8 mmol) were dissolved in THF (10 mL), p-toluenesulfonic acid (p-TsOH, 10 mg) was added, and the mixture was stirred at room temperature for 15 hr. Triethylamine (1 mL) was poured into the reaction mixture and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate (0.5 g) and filtered. The solvent was evaporated to give the corresponding ethyl (S)-3-methoxymethoxytetradecanoate (2.20 g, yield 95%). the mixture was washed with saturated aqueous sodium hydrogencarbonate solution (10 mL) and saturated brine (10 mL) dried over anhydrous magnesium sulfate (0.5 g) filtered The solvent was evaporated