Water → 2-Methyl-1-(4-nitrophenyl)propane-1,2-diol

Participants

Reaction Steps

To a solution of N-methyl morpholine-N-oxide (1.5 g, 12.8 mmol) in 4.5 mL of water was added a solution of tert-butyl 1-(2-methylprop-1-enyl)-4-nitrobenzene (1.5 g, 8.5 mmol) in acetone/water (5:1, 36 mL), followed by the addition of a solution of osmium tetraoxide in water (2 mL, 4%). This mixture was allowed to RT and stirred for 16 h. The reaction was quenched by sat. Na2SO3. aq (100 mL) and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuo. The crude product (1.7 g, yield 100%) was obtained as a yellow foam, which was directly used into the next step without further purification. 1H-NMR (400 MHz, CDCl3) δ ppm 8.20 (d, 2H, J=9.2 Hz), 7.57 (d, 2H, J=9.2 Hz), 4.63 (d, 1H, J=2.4 Hz), 2.69 (d, 1H, J=3.2 Hz), 2.03 (d, 1H, J=3.2 Hz), 1.19 (s, 3H), 1.08 (s, 3H).

Provenance & Evidence