反应详情

Sodium hydride (0.257 g, 6.4 mmol) was added to 6-(4-hydroxy-3,5-diisopropyl-phenyl)-hexanoic acid ethyl ester (1.46 g, 5.0 mmol) in dimethylformamide (20 mL) at 0° C. over about 3 minutes. The cooling bath was removed, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to zero degrees and sulfamoyl chloride (1.18 g, 10.3 mmol) was added over ~ 3 minutes. The reaction mixture was stirred 1.5 hours at zero degrees and was quenched by adding saturated aqueous sodium bicarbonate solution. The mixture is diluted with diethyl ether (300 mL) and water (100 mL). The organic layer is washed with water (3×100 mL), brine, dried over magnesium sulfate, filtered, and concentrated to an oil. The oil is chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant. The title compound is obtained as a light yellow oil, 1.29 g. CI Mass Spectrum: [M+H+ ]+ =400.

1. customThe cooling bath was removed
2. temperatureThe reaction mixture was cooled to zero degrees
3. stirringThe reaction mixture was stirred 1.5 hours at zero degrees
4. customwas quenched
5. additionby adding saturated aqueous sodium bicarbonate solution
6. additionThe mixture is diluted with diethyl ether (300 mL) and water (100 mL)
7. washThe organic layer is washed with water (3×100 mL), brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated to an oil
11. customThe oil is chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant