反应详情

To a cooled solution of 0.997 mL of 1M boron tribromide (0.9 mmol) in 2 mL dichloromethane, 0.150 g (0.433 mmol) of 5-[2-(3,4-dimethoxy-phenyl)-vinyl]-3-octyl-[1,2,4]oxadiazole (compound of Example 48) dissolved in 1 mL of dichloromethane was added over a period of 15-20 min at −45° C. to −40° C. The reaction mixture was stirred at −45° C. to −40° C. for 30-45 min and allowed to attain 25° C. to 30° C. slowly, over a period of 1 h. The reaction mass was further stirred at 25° C. to 30° C. for 4-5 h. After completion of the reaction, the reaction mixture was quenched in 10 mL of chilled 5% sodium bicarbonate solution, below 20° C. (pH: 8-9). 10 mL of ethyl acetate was added to the reaction mixture to dissolve the solid and stirred for 10-15 min. The organic layer was separated and the aqueous layer was washed with 10 mL of 10% sodium chloride solution. The organic layer was collected and distilled to obtain a crude residue, which was purified by column chromatography (silica gel, chloroform-methanol) to yield the title compound.

1. additionwas added over a period of 15-20 min at −45° C. to −40° C
2. customto attain 25° C. to 30° C.
3. waitover a period of 1 h
4. stirringThe reaction mass was further stirred at 25° C. to 30° C. for 4-5 h
5. customAfter completion of the reaction
6. customthe reaction mixture was quenched in 10 mL of chilled 5% sodium bicarbonate solution, below 20° C. (pH: 8-9)
7. addition10 mL of ethyl acetate was added to the reaction mixture
8. dissolutionto dissolve the solid
9. stirringstirred for 10-15 min
10. customThe organic layer was separated
11. washthe aqueous layer was washed with 10 mL of 10% sodium chloride solution
12. customThe organic layer was collected
13. distillationdistilled
14. customto obtain a crude residue, which
15. customwas purified by column chromatography (silica gel, chloroform-methanol)