Potassium Carbonate → Ethyl 3-{4-chloro-3-[(2S)-oxiran-2-yl]phenyl}propanoate

Participants

Reaction Steps

To a solution of ethyl 3-[4-chloro-3-((1S)-1-hydroxy-2-{[(4-methylphenyl) sulfonyl]oxy}ethyl)phenyl]propanoate (1.77 g, 4.1 mmol) in absolute ethanol (12 mL) was added potassium carbonate (0.63 g, 4.6 mmol) and the reaction was stirred at rt for 3 days. The reaction was concentrated and diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with H2O, brine, dried (Na2SO4), and concentrated to afford 810 mg of product as a white solid (78%). The product was pure enough to use in the subsequent step. 1H NMR (400 MHz, chloroform-d) δ ppm 7.27 (d, J=8.59 Hz, 1 H) 7.07-7.10 (m, J=2.72, 2.72, 2.72, 2.72 Hz, 2 H) 4.19 (dd, J=4.04, 2.53 Hz, 1 H) 4.13 (q, J=7.07 Hz, 2 H) 3.19 (dd, J=5.68, 4.17 Hz, 1 H) 2.91 (t, J=7.71 Hz, 2 H) 2.65 (dd, J=5.56, 2.53 Hz, 1 H) 2.59 (t, J=7.58 Hz, 2 H) 1.24 (t, J=7.20 Hz, 3 H)

Provenance & Evidence