反应详情

5-Hydroxy-1H-indole (500 mg, 3.76 mmol) and allyl bromide (499.7 mg, 4.13 mmol) were dissolved in DMF (15 mL), then Cs2CO3 (1.468 g, 4.51 mmol), and water (6 drops) were added. The reaction mixture was stirred at rt for 12 h, after which it was concentrated under reduced pressure, diluted with water, and the aqueous layer was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:11) gave 514 mg (79%) of the title compound as a light-yellow oil. 1H NMR (400 MHz, CDCl3): δ 4.59 (d, 2H), 5.29 (d, 1H), 5.45 (d, 1H), 6.12 (m, 1H), 6.48 (d, 1H), 6.90 (d, 1H), 7.11 (s, 1H), 7.19 (s, 1H), 7.28 (m, 1H), 8.04 (br, 1H).

1. concentrationafter which it was concentrated under reduced pressure
2. additiondiluted with water
3. extractionthe aqueous layer was extracted with EtOAc (2×)
4. dry with materialThe combined organic phases were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:11)