2-(2-((tert-butyldiphenylsilyl)oxy)ethoxy)ethanol(WXPC0004) synthesis

Yield:160052-24-4 80%

Reaction Conditions:

with pyridine at 0 - 20; for 1 h;

Steps:

34.1 Step 1: Synthesis of 2-[2-[tert-butyl(diphenyl)silyl]oxyethoxy]ethanol:

To a solution of 2-(2-hydroxyethoxy)ethanol (50 g, 471.2 mmol) in pyridine (49.6 mL) at 0 °C was added tert-butyl-chloro-diphenyl-silane (30 g, 109.2 mmol). The resulting solution was stirred at rt for 1h then poured into water (300 mL) and extracted with EtOAc (300mL × 3). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc:PE = 1:8) to provide 2-[2-[tert-butyl(diphenyl)silyl]oxyethoxy]ethanol (29.9 g, 80% yield) as a colorless oil. ESI-MS (EI⁺, m/z): 367.2 [M+Na]⁺. ¹H NMR (400 MHz, CDCl3) d 7.74- 7.64 (m, 4H), 7.46- 7.33 (m, 6H), 3.81 (t, J = 5.2 Hz, 2H), 3.73- 3.66 (m, 2H), 3.63- 3.54 (m, 4H), 2.32 (d, J = 3.5 Hz, 1H), 1.06 (s, 9H).

References:

WO2019/241789,2019,A1 Location in patent:Paragraph 00467-00468