The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 2050-25-1
Step 1. 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)acetonitrile. To a stirring solution of diethylene glycol benzyl ether (1.0 g, 5.1 mmol) in THF (10 mL) at 0 C, was added in small portions NaH (408 mg, 10.2 mmol), then the reaction mixture was warmed to rt and stirred for 30 mins. The reaction mixture was cooled to 0 C, and bromoacetonitrile (0.39 mL, 5.6 mmol) was added dropwise and stirred for 3h. The reaction was quenched with saturated ammonium chloride, and extracted with EtOAc (3 x 50 mL). The combined organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was further purified by silica gel chromatography using 25% acetone/hexanes eluent to afford 2-(2-(2-(benzyloxy)ethoxy)ethoxy)acetonitrile as a colorless oil (437 mg, 37%): XH NMR (500MHz, CDC13) delta ppm 7.35 (d, J= 4.9 Hz, 4H), 7.27 – 7.32 (m, 1H), 4.57 (s, 2H), 4.33 (s, 2H), 3.76 – 3.80 (m, 2H), 3.67 – 3.74 (m, 4H), 3.62 – 3.66 (m, 2H).
The synthetic route of 2050-25-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); A1;,
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