Acetone → Ethyl (3-bromo-1,4-naphthoquinon-2-yl)-propionate

Following the general procedures by Shinkawa et al. and Flader et al.,16,22 67a (0.361 g, 0.983 mmol) was dissolved in EtOAc (10.0 mL) and then AcOH (6 drops) and HNO3 (1.0 mL) were added at room temperature. Then Ag(II)O (0.473 g, 3.82 mmol) was added in one portion at room temperature and stirred for 30 minutes at room temperature, the reaction was monitored by TLC (1:4 acetone:hexanes). After 30 minutes another addition of Ag(II)O (0.147 g, 1.19 mmol) was required, and the reaction stirred at room temperature for another 30 minutes. TLC showed the reaction to be complete, and the solvent was then separated from the silver solid by passing the reaction through a pipette with cotton plug, the solid was rinsed with EtOAc (4×5.0 mL), and then the solution was diluted with EtOAc (50.0 mL). The solution was then washed 2 times with saturated brine, dried over MgSO4, filtered, and condensed. The crude yellow solid was recrystallized from acetone/hexane to provide 68a (0.135 g, 0.400 mmol, 41%) as a yellow solid.

1. stirringthe reaction stirred at room temperature for another 30 minutes
2. customthe reaction
3. customthe solvent was then separated from the silver solid
4. customthe reaction through a pipette with cotton plug
5. washthe solid was rinsed with EtOAc (4×5.0 mL)
6. additionthe solution was diluted with EtOAc (50.0 mL)
7. washThe solution was then washed 2 times with saturated brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customcondensed
11. customThe crude yellow solid was recrystallized from acetone/hexane

ORD record

ord-ecbdfa607e0c49949d81658c37b1cb5e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09089605B2