Imidazole → (R)-ethyl 5-((tert-butyldiphenylsilyl)oxy)hexanoate

Participants

Reaction Steps

To a solution of (R)-ethyl 5-hydroxyhexanoate (5 g, 31.2 mmol) in DMF (100 mL) at 0° C. was added imidazole (3.19 g, 46.8 mmol) followed by tert-butylchlorodiphenylsilane (12.00 mL, 46.8 mmol) and the resulting mixture was stirred at room temp for 16 h. Water (30 mL) was then added and the mixture was extracted with ether (2×100 mL). Ether layer was then washed with brine (50 mL), dried (Na2SO4), filtered and concentrated. The residue was purified via Biotage (0-10% EtOAc/hexane) to afford (R)-ethyl 5-((tert-butyldiphenylsilyl)oxy)hexanoate (10 g, 25.09 mmol, 80% yield) as clear viscous liquid. 1H NMR (500 MHz, CDCl3) δ 7.73-7.68 (m, 4H), 7.48-7.36 (m, 6H), 4.13 (q, J=7.2 Hz, 2H), 3.96-3.76 (m, 1H), 2.31-2.16 (m, 2H), 1.72-1.62 (m, 2H), 1.58-1.40 (m, 2H), 1.27 (t, J=7.1 Hz, 3H), 1.12-1.05 (m, 12H).

Provenance & Evidence