反应详情

NaH (0.20 g; 8.14 mmol) was added to a room temperature solution of 3,4-dihydroxybenzonitrile (1.00 g; 7.40 mmol) in DMF. After stirring for 15 minutes, 1-bromo-3-chloropropane (1.3 g; 8.14 mmol) was added to the mixture. The reaction was stirred for 40 h at room temperature, and then quenched with water and extracted with EtOAc (100 mL). The EtOAc extract was washed with brine (4×100 mL), dried over Na2SO4 and concentrated in vacuo. The resulting crude product was chromatographed on a column of silica (5 cm×18 cm) eluting with a mixture of EtOAc and hexanes (1:4). Fractions containing the desired product were combined and concentrated in vacuo to afford the sub-title compound as an oil (0.5 g; 32%).

1. stirringThe reaction was stirred for 40 h at room temperature
2. customquenched with water
3. extractionextracted with EtOAc (100 mL)
4. extractionThe EtOAc extract
5. washwas washed with brine (4×100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe resulting crude product was chromatographed on a column of silica (5 cm×18 cm)
9. washeluting with a mixture of EtOAc and hexanes (1:4)
10. additionFractions containing the desired product
11. concentrationconcentrated in vacuo