反应详情

A solution of hydroxylamine sulfate (976 mg, 5.947 mmol) in water (4 mL) is added to a stirred solution of 5-methoxy-4,4-dimethyl-3-oxo-pentanenitrile (1.678 g, 10.812 mmol) and sodium hydroxide (490.3 mg, 11.89 mmol) in water (13 mL). The reaction mixture is heated to reflux over 30 minutes and kept at reflux for 1 hour. After cooling, 37% HCl aqueous solution (0.8 mL, 9.73 mmol) is added and the mixture is heated to reflux for 20 minutes. After cooling, the mixture's pH is adjusted to ˜12 by adding 40% sodium hydroxide aqueous solution. The mixture is extracted with methylene chloride 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 171 [M+H+].

1. temperatureThe reaction mixture is heated
2. temperatureto reflux over 30 minutes
3. temperatureat reflux for 1 hour
4. temperatureAfter cooling
5. temperaturethe mixture is heated
6. temperatureto reflux for 20 minutes
7. temperatureAfter cooling
8. extractionThe mixture is extracted with methylene chloride 3 times
9. washwashed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customPurification by flash chromatography on silica gel