反应详情

A cooled (0° C.) suspension of NaH (20.61 mg; 0.52 mmol; 1.00 eq.) in dry DMF was carefully treated with solution of 6-bromo-2,2-dimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide (Intermediate 244; 150 mg; 0.52 mmol) in anhydrous DMF. The reaction mixture was stirred at RT for 4 min then treated with a 3 M solution of iodomethane (240 μl; 0.72 mmol). The mixture was stirred at RT for 2.5 h, then quenched with water. EtOAc was added, the phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate and concentrated to dryness to afford a residue, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as a white solid.

1. temperatureA cooled
2. stirringThe mixture was stirred at RT for 2.5 h
3. customquenched with water
4. additionEtOAc was added
5. customthe phases were separated
6. extractionthe aqueous phase was extracted with EtOAc
7. washThe combined organic phases were washed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated to dryness
10. customto afford a residue, which
11. customwas purified by flash column chromatography (silica)
12. washeluting with cyclohexane containing
13. temperatureincreasing amounts of EtOAc