Reacción #88059

Ecuación de reacción

benzylmagnesium chloride

water

4-(2-phenyl-chroman-6-yloxy)-cyclohexanone

tert-butylsulfinamide

benzylmagnesium chloride

→

2-methyl-propane-2-sulfinic acid [1-benzyl-4-(2-phenyl-chroman-6-yloxy)-cyclohexyl]-amide

Rendimiento 43.5%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting solution heated
2. 2
   Temperaturato reflux for 16 h
3. 3
   workup.STIRRINGAfter additional 16 h of stirring the reaction
4. 4
   FiltraciónThe suspension was filtered
5. 5
   Lavadothe filter cake washed with dichloromethane
6. 6
   ExtracciónThe aqueous layer was extracted with dichloromethane
7. 7
   SecadoThe combined organic layers were dried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Otrothe solvent removed by evaporation
10. 10
    OtroThe resulting oil was purified by chromatography over silica gel using a heptane/ethyl acetate gradient (0% ethyl acetate to 25% ethyl acetate)

Procedimiento

To a solution of 352 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanone (1.1 mmol) in 10 ml of tetrahydrofuran at room temperature 0.46 ml of titanium(IV) ethoxide (2.18 mmol) and 139 mg of tert-butylsulfinamide (1.15 mmol) were added and the resulting solution heated to reflux for 16 h. The solution was cooled to 0° C. and 1.09 ml of benzylmagnesium chloride (2M in tetrahydrofuran, 2.18 mmol) were added. The mixture was stirred at room temperature for 16 h and additional 1.09 ml of benzylmagnesium chloride solution were added. After additional 16 h of stirring the reaction was stopped by careful addition of water. The suspension was filtered and the filter cake washed with dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and filtered, and the solvent removed by evaporation. The resulting oil was purified by chromatography over silica gel using a heptane/ethyl acetate gradient (0% ethyl acetate to 25% ethyl acetate). 248 mg of 2-methyl-propane-2-sulfinic acid [1-benzyl-4-(2-phenyl-chroman-6-yloxy)-cyclohexyl]-amide were isolated as a mixture of diastereomers (44%).

Fuente