反应详情

Molybdenum hexacarbonyl (98%, 6.67 g, 24.8 mmol) was added to a solution of C3 (15.12 g, 49.54 mmol) in a mixture of acetonitrile (390 mL) and water (20 mL), and the reaction mixture was heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was chilled in an ice bath, treated portion-wise with sodium borohydride (7.50 g, 198 mmol), and allowed to stir at 0° C. for 1 hour. The mixture was then filtered through a pad of diatomaceous earth, and the pad was washed three times with dichloromethane; the organic portion of the combined filtrate and washes was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Methanol was added to the residue, then removed via concentration under reduced pressure. This methanol treatment was repeated, and the resulting residue was dissolved in dichloromethane, washed twice with 1 M aqueous sodium hydroxide solution, washed once with saturated aqueous sodium chloride solution and concentrated in vacuo, affording the product as a brown solid. Yield: 14.48 g, 47.13 mmol, 95%. LCMS m/z 307.0, 309.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H), 3.79 (d, half of AB quartet, J=11.5 Hz, 1H), 3.64-3.75 (m, 3H), 3.54 (dd, half of ABX pattern, J=11.5, 4.1 Hz, 1H), 2.46-2.54 (m, 1H), 1.82-1.94 (m, 1H), 1.67-1.74 (m, 1H), 1.32 (d, J=6.2 Hz, 3H).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 1 hour
3. temperaturethe reaction mixture was chilled in an ice bath
4. filtrationThe mixture was then filtered through a pad of diatomaceous earth
5. washthe pad was washed three times with dichloromethane
6. washthe organic portion of the combined filtrate and washes was washed with saturated aqueous sodium chloride solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. additionMethanol was added to the residue
11. customremoved via concentration under reduced pressure
12. dissolutionthe resulting residue was dissolved in dichloromethane
13. washwashed twice with 1 M aqueous sodium hydroxide solution
14. washwashed once with saturated aqueous sodium chloride solution
15. concentrationconcentrated in vacuo