反应详情

To a suspension of 0.10 g (4.59 mmol) of lithium borohydride in 3 mL THF was carefully added 1.3 mL (10.2 mmol) of chlorotrimethylsilane. The reaction mixture was stirred for 2 min and then a solution of 0.367 g (1.0 mmol) of 1-(benzyloxy)-3,5-di-tert-butyl-2-[2-nitrovinyl]benzene from Step B of Example 75 dissolved in 1.5 mL of anhydrous THF was slowly added. The resulting reaction mixture was stirred overnight at room temperature then cooled using an external ice water bath and 15 mL of methanol was slowly added. The resulting mixture was evaporated in vacuo, the residue was the treated with 20 mL of 5 N aqueous sodium hydroxide and then the reaction mixture was extracted with 5 times with 20 mL portions of CH2Cl2. The combined extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted initially with 5% MeOH in CH2Cl2 followed by a 95/5/0.5 mixture of CH2Cl2—MeOH-conc. NH4OH. Combination of the purified fractions and evaporation in vacuo afforded the title compound.

1. additionwas slowly added
2. customThe resulting reaction mixture
3. stirringwas stirred overnight at room temperature
4. temperaturethen cooled
5. customThe resulting mixture was evaporated in vacuo
6. additiontreated with 20 mL of 5 N aqueous sodium hydroxide
7. extractionthe reaction mixture was extracted with 5 times with 20 mL portions of CH2Cl2
8. dry with materialThe combined extracts were dried (Na2SO4)
9. filtrationfiltered
10. customevaporated in vacuo
11. customThe residue was purified on a silica gel flash chromatography column
12. washeluted initially with 5% MeOH in CH2Cl2
13. additionfollowed by a 95/5/0.5 mixture of CH2Cl2—MeOH-conc
14. customCombination of the purified fractions and evaporation in vacuo