反应详情

n-Butyllithium (a 1.42M solution in hexane, 2.33 ml, 3.31 mmol) was added to a solution of 1-methylpiperazine (331 mg. 3.31 mmol) in tetrahydrofuran (15 ml) at 0 degrees under argon. After 15 minutes the solution was cooled to -78 degrees and 4-phenyl-3-furaldehyde (517 mg, 3.01 mmol) was added. This mixture was warmed to 0 degrees and stirred for 15 minutes, then recooled to -78 degrees before sec-butyllithium (a 1.3M solutin in cyclohexane, 2.77 ml, 3.61 mmol) was added dropwise. This solution was stirred 12 hours at -78 degrees C. before chlorotriethylsilane (1.81 g, 12.02 mmol) was added. The mixture was allowed to warm gradually to room temperature and stirred an additional 11/2 hours. The reaction was quenched with ice-cold 5% (V/V) hydrochloric acid and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 10% ethyl acetate/hexanes to give the title aldehyde.

1. temperatureAfter 15 minutes the solution was cooled to -78 degrees
2. temperatureThis mixture was warmed to 0 degrees
3. additionwas added dropwise
4. stirringThis solution was stirred 12 hours at -78 degrees C
5. stirringstirred an additional 11/2 hours
6. customThe reaction was quenched with ice-cold 5% (V/V) hydrochloric acid
7. extractionthe organics were extracted into ethyl ether
8. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
9. customEvaporation of the
10. dry with materialdried (magnesium sulfate)
11. customextracts gave an oil which
12. customwas purified by flash chromatography on silica using 10% ethyl acetate/hexanes