反应详情

温度

0 °C

(R)-1-[4-(Benzyloxy)-3-nitrophenyl]-2-bromoethanol (0.2 g, 5.7 mmol) in THF:toluene (1:1, 5 mL) was reacted with PtO2 (1% w/w) on a Parr shaker at 45 psi at rt overnight. The next morning the PtO2 was removed by filtration over celite. The filtered solution was cooled to 0° C. and a solution of acetic anhydride (0.161 mL, 0.569 mmol) and formic acid (0.043 mL, 1.140 mmol) was added dropwise to a stirred solution. After 30 min the reaction was warmed to rt and stirred for 2 h. The reaction mixture was concentrated to near dryness and water was added. The aqueous layer was extracted with EtOAc (3×25 mL). The combined organic layers were washed with NaHCO3, brine, dried over Na2SO4 (s), and concentrated. Chromatography (1:1 Hexanes/EtOAc) gave the title compound (156 mg, 78% 2 steps). ES/MS calcd. C16H17BrNO3+ 350.0. Found m/z=350 (M+H)+.

1. customThe next morning the PtO2 was removed by filtration over celite
2. temperatureAfter 30 min the reaction was warmed to rt
3. concentrationThe reaction mixture was concentrated
4. additionwas added
5. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
6. washThe combined organic layers were washed with NaHCO3, brine
7. dry with materialdried over Na2SO4 (s)
8. concentrationconcentrated