Hydrogen Peroxide → HCID 52943384, compound

Participants

Reaction Steps

BH3.THF (162 μL, 0.162 mmol) was added dropwise via syringe to a solution of 1 (50 mg, 0.108 mmol) in anhydrous THF (6 mL). The reaction mixture was stirred at ambient temperature for 1 h. 5% aqueous NaOH (0.5 mL) and 30% aqueous H2O2 (1 mL) were added and the reaction mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was extracted with EtOAc and the organic layers were pooled, washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil. The oil was purified by flash chromatography (silica gel, 40% EtOAc/hexane) to yield a yellow oil. The oil was triturated in (1:1) Et2O/hexane to provide a white solid. 1H NMR (DMSO-d6) δ 0.89 (t, J=7.2 Hz, 3H), 1.21 (t, J=7.0 Hz, 3H), 1.78 (m, 2H), 3.18 (m, 2H), 3.40 (m, 2H), 3.50 (m, 6H), 3.72 (m, 4H), 4.16 (q, J=7.1 Hz, 2H), 4.45 (t, J=5.3 Hz, 1H), 6.77 (s, 1H), 7.41 (m, 2H), 7.46 (m, 3H). Mass Spectrum (ESI+) m/e=482.2 (M+H).

Provenance & Evidence