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• Synthesis

  

  General synthetic method: Under argon protection, iodoalkane (1 eq.) was added to a DMF (40 mL) solution containing triethylene glycol or tritetraethylene glycol (1 eq.). The mixture was cooled to 0 °C, and sodium hydride (1.5 eq. 60% in mineral oil) was added. The mixture was stirred for 2 h, quenched with water, and extracted with ethyl acetate (20 mL × 2). The ethyl acetate phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate-n-hexane). The sample was immediately used for the next reaction.

  The synthesis of lauryl ether-4 was carried out using the general synthetic method described above. Tetraethylene glycol (2 mL, 11.59 mmol) was reacted with 1-iodododecane (4.42 g, 11.59 mmol) and sodium hydride (0.70 g, 17.38 mmol) to give lauryl ether-4 (2.18 g, 6.02 mmol, yield 52%), a colorless oil; Rf = 0.41 (ethyl acetate-n-hexane 3:2).;

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