tert-Butyl hydroperoxide → HCID 68871675, compound

Participants

Reaction Steps

To a solution of the product of Example 169B (190 mg, 0.63 mmol) in benzene (4 mL) at room temperature under a N2 atmosphere was added 200 mg Celite® and pyridinium dichromate (474 mg, 1.26 mmol) followed by 70% tert-butyl hydroperoxide (175 μL, 1.26 mmol). The mixture was allowed to stir at room temperature for 1 hour, filtered through a pad of Celite® and the filtrate added to ethyl acetate (10 mL). The organic solution was washed with 5% Na2S2O5 (3× 10 mL) and with saturated NaCl (1× 10 mL) and dried over Na2SO4. The crude product was purified by column chromatography using 50% ethyl acetate in hexane. The title compound was obtained as a colorless oil (59 mg, 30%). 1H NMR (300 MHz, CDCl3): δ 8.18 (d, 1H), 7.56 (t, 1H), 7.44 (t, 1H), 7.26 (d, 1H), 5.98 (s, 1H), 3.85 (s, 3H), 2.95, 2.39 (dm, 3H), 2.42, 2.21 (dm, 2H), 1.56 (s, 3H), 1.32 (m, 1H), 0.73 (d, 3H), 0.65 (d, 3H), 0.28 (m, 2H). MS (ESI) m/z=316 [M+H].

Provenance & Evidence