Sodium Hydroxide → HCID 16065088, compound

Participants

Reaction Steps

To a stirred solution of 76 (155 mg, 0.31 mmol) in EtOH (4 mL) was added 10% aqueous NaOH (2 mL) and the reaction was heated at reflux for 1.5 h. The mixture was then cooled. Saturated aqueous NaHCO3 (25 mL) was added, and the solution was extracted with AcOEt (2×40 mL) The combined organic extracts were dried (MgSO4) and concentrated to afford a brown solid, which was purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 77 as a white solid (54 mg, 0.15 mmol, 49%). 1H NMR (400 MHz, CDCl3) δ 0.96 (d, J=6.6 Hz, 2H), 1.94 (nonet, J=6.7 Hz, 1H), 2.07-2.19 (m, 2H), 2.25-2.35 (m, 2H), 2.41-2.52 (m, 5H), 2.64 (d, J=7.1 Hz, 2H), 3.14-3.24 (m, 3H), 7.26 (s, 1H), 7.83 (s, 1H), 8.10 (d, J=1.9 Hz, 1H), 8.18 (d, J=1.9 Hz, 1H), 10.90 (br s, 1H). MS (CI) m/z 355 (MH+).

Provenance & Evidence