反应详情

To a chilled solution (ice-water bath) of 6 g (17.0 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 60 mL of dry THF, 2.4 g (61.5 mmol) of lithium aluminum hydride was added in portions. After the addition, the cold bath was removed and the mixture was stirred at room temperature overnight. The mixture was then warmed at reflux for 3 hours and then cautiously quenched by slow addition to 100 mL of THF containing 2 mL of water. Additional water was then cautiously added for a total of 15 mL and the resulting mixture stirred for 2 hours. The excess water was dried with magnesium sulfate and 300 mL of EtOAc was added. After 1 hour, the mixture was filtered through diatomaceous earth and concentrated in vacuo to afford 4.9 g (92%) of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol as an oil.

1. additionAfter the addition
2. customthe cold bath was removed
3. temperatureThe mixture was then warmed
4. temperatureat reflux for 3 hours
5. customcautiously quenched by slow addition to 100 mL of THF containing 2 mL of water
6. additionAdditional water was then cautiously added for a total of 15 mL
7. stirringthe resulting mixture stirred for 2 hours
8. dry with materialThe excess water was dried with magnesium sulfate and 300 mL of EtOAc
9. additionwas added
10. waitAfter 1 hour
11. filtrationthe mixture was filtered through diatomaceous earth
12. concentrationconcentrated in vacuo