Water → HCID 86682289, compound

Participants

Reaction Steps

To a 100 mL RBF were added 2-bromo-4-(cyclopent-3-en-1-yl)-1-methoxybenzene (1.9 g, 7.51 mmol), NMO (2.64 g, 22.5 mmol), osmium tetroxide (0.942 mL, 0.075 mmol, 2.5% in t-BuOH), t-butanol (13 mL) and water (13 mL). The resulting reaction mixture was stirred at rt over the weekend. Volatiles were removed. Crude material was dissolved in 100 mL EtOAc and washed with 50 mL water. Organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 80% EtOAc in hexane to give 4-(3-bromo-4-methoxyphenyl)cyclopentane-1,2-diol (1.7 g) as white solid. 1H NMR (500 MHz, CDCl3): δ 7.39 (s, 1H), 7.10 (d, 1H), 6.85 (d, 1H), 4.37 (m, 2H), 3.91 (s, 3H), 3.55 (m, 1H), 2.46 (b, 2H), 2.18 (m, 2H), 1.88 (m, 2H).

Provenance & Evidence