反应详情

Under nitrogen, n-butyllithium (5.6 mL of a 2.5M hexane solution) was added dropwise, to a -78° C. solution of the 2,4,5,7-tetrafluorofluorene in gold label THF (80 mL) over 2 min. After 20 min, the mixture was poured onto a slurry of dry-ice (10 g) in anhydrous ether. The solvents were evaporated and the residue was dissolved in methanol (200 mL) and acidified with acetyl chloride (5 mL). After stirring for 18 h, the reaction was concentrated and the residue was diluted with saturated aqueous sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine (3×100 mL), dried (MgSO4), and evaporated. The residue was chromatographed on silica gel using petroleum ether to provide 2.1 g (57%) of product: 1H NMR (DMSO-d6, 200 MHz) δ7.44 (dd, 2H, J=2.2 and 8.3 Hz), 7.40-7.25 (m, 2H), 5.37 (s, 1H), 3.76 (s, 3H).

1. customThe solvents were evaporated
2. dissolutionthe residue was dissolved in methanol (200 mL)
3. concentrationthe reaction was concentrated
4. additionthe residue was diluted with saturated aqueous sodium bicarbonate (200 mL)
5. extractionextracted with ethyl acetate (3×100 mL)
6. washThe combined organics were washed with brine (3×100 mL)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customThe residue was chromatographed on silica gel