1,2-Dichloroethane → 3-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-ethoxy-propionic acid 2,2,2-trichloro-ethyl ester

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Reaction Steps

Under nitrogen atmosphere 3-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-2-ethoxy-propionic acid (0.135 g, 0.4 mmol) and 2,2,2-trichloro ethanol (0.06 g, 0.4 mmol) were dissolved in dry DCM (5 mL) and DMAP (2 mg, 0.02 mmol) was added followed by EDC×HCl (0.092 g, 0.48 mmol) at 0° C. The mixture was stirred for 18 h at ambient temperature, then diluted with DCM and extracted with aq. HCl (2N) and water. The organic layer was separated, dried (MgSO4) and evaporated to afford the crude product which was used in the next step without further purification (0.176 g, 93.6%). 1H NMR (400 MHz, CDCl3): δ 7.12-7.19 (m, 4H), 4.62-4.71 (q, 2H), 4.63 (s, 2H), 4.05-4.08 (m, 1H), 3.55-3.59 (m, 1H), 3.27-3.31 (m, 1H), 2.92-3.03 (m, 2H), 1.08 (t, 3H).

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