反应详情

To a mixture of trans-6,13-dihydroxy-6,13-dihydropentacene (1.0 g, 3.20 mmol) and zinc iodide (1.02 g, 3.20 mmol) were added successively dry CH2Cl2 (100 mL) and phenethylthiophenol (0.77 g, 7.03 mmol) at RT under an argon atmosphere. The resulting mixture was stirred at RT for 2 h, and then quenched with H2O. The mixture was extracted with CH2Cl2, and the organic layer was washed with brine and dried over anhyd. Na2SO4. After evaporation of solvents, the residue was purified by column chromatography on silica gel eluted with n-hexanes-CH2Cl2 (2:1) to give product as white solids in 71% yield (1.13 g). 1H NMR (500 MHz, CDCl3): δ 7.80 (m, 4H), 7.70 (s, 4H), 7.46 (m, 4H), 7.29 (t, 4H, J=7.56 Hz), 7.20 (m, 6H), 5.24 (s, 2H), 2.90 (s, 8H). LDI-MS m/z: 552 [M+], 416 [M+-SCH2CH2C6H5], 280 [M+-2(SCH2CH2C6H5)].

1. customquenched with H2O
2. extractionThe mixture was extracted with CH2Cl2
3. washthe organic layer was washed with brine
4. customdried over anhyd
5. customAfter evaporation of solvents
6. customthe residue was purified by column chromatography on silica gel
7. washeluted with n-hexanes-CH2Cl2 (2:1)
8. customto give product as white solids in 71% yield (1.13 g)