反应详情

温度

35 °C

1.5M n-BuLi in hexane (53 mL, 80 mmol) was added in small portions to a solution of 2,3-dihydrothieno[3,4-b][1,4]dioxine (10.00 g, 80 mmol) and tetramethylethylenediamine (12.0 mL, 80 mmol) in tetrahydrofuran (100 mL) stirred under argon and cooled in a dry ice/acetone bath. The reaction mixture was heated to 35° C., stirred at this temperature for 1 hour, and then cooled in a dry ice/acetone bath. Tributylstannyl chloride (20.3 mL), 75 mmol was then added, the mixture was allowed to warm up, and it was left at room temperature for 16 hours. The volatiles were removed under reduced pressure. The residue was diluted with toluene (100 mL) and chromatographed using a column filled with silica gel (500 mL) washed with 2% triethylamine in hexane (500 mL) to give tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane (12.17 g, 40%) of high purity. 1H NMR (400 MHz, CDCl3): δ 6.57 (s, 1H, thiophene), 4.15 (m, 4H, OCH2CH2O), 1.53 (m, 6H, Bu), 1.32 (quintet, J=7.3 Hz, 6H, Bu), 1.09 (m, 6H, Bu), 0.88 (t, J=7.3 Hz, 9H, Bu).

1. temperaturecooled in a dry ice/acetone bath
2. stirringstirred at this temperature for 1 hour
3. temperaturecooled in a dry ice/acetone bath
4. temperatureto warm up
5. customThe volatiles were removed under reduced pressure
6. additionThe residue was diluted with toluene (100 mL)
7. customchromatographed
8. additionfilled with silica gel (500 mL)
9. washwashed with 2% triethylamine in hexane (500 mL)