反应详情

Isoprene monoxide (2.64 g, 31.40 mmol) of Chemical Formula 2 was mixed with DMF (30 mL) and stirred, and the resulting stirred solution was added with 2-mercaptobenzothiazole (5.25 g, 31.40 mmol) and CuI (299 mg, 1.57 mmol). The reaction mixture was stirred at room temperature for 21 hr, and added with a 1 M HCl solution to terminate the reaction, and the resulting reaction product was diluted with CH2Cl2. The unreacted yellow starting material was removed using a porous glass funnel filter, and the filtrate was washed with a 1 M NaOH solution and H2O, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure, thus obtaining a crude product. The crude product was analyzed with 1H-NMR, yielding a 1,2-addition product (0.68 g, 2.71 mmol, 9% yield, Rf=0.31/1:4 EtOAc/hexane), a 1,4-addition product (Z-configuration, 0.85 g, 3.38 mmol, 11% yield, Rf=0.24/1:4 EtOAc/hexane), and a 1,4-addition product (E-configuration, Chemical Formula 3, 3.40 g, 13.53 mmol, 43% yield, Rf=0.15/1:4 EtOAc/hexane) at a ratio of 1:1.25:5 from the sulfide.

1. stirringthe resulting stirred solution
2. stirringThe reaction mixture was stirred at room temperature for 21 hr
3. customto terminate
4. customthe reaction
5. customthe resulting reaction product
6. customwas removed
7. filtrationfilter
8. washthe filtrate was washed with a 1 M NaOH solution and H2O
9. dry with materialdried over anhydrous Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customthus obtaining a crude product