反应详情

n-Butyllithium (a 1.6m solution in hexane, 2.43 ml, 3.89 mmol) was added to a solution of trimethylethylenediamine (397 mg, 3.89 mmol) in tetrahydrofuran (25 ml) at 0 degrees under argon. After 20 minutes the solution was cooled to -78 degres and 4-phenyl-3-furaldehyde (608 mg, 3.35 mmol) was added. This mixture was allowed to gradually warm to -20 degrees and stirred for 11/2 hours, then recooled to -78 degrees before n-butyllithium (a 1.6M solution in hexane, 2.43 ml, 3.89 mmol) was added dropwise. The stirring mixture was again gradually warmed to -20 degrees and stirred for 2 hours before iodomethane (2.56 g 17.67 mmol) was added. After stirring for 18 hours at -20 degrees the reaction was quenched with ice-cold 10% (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 20% ethyl ether/hexanes to give the title aldehyde.

1. additionwas added
2. temperatureto gradually warm to -20 degrees
3. additionwas added dropwise
4. temperatureThe stirring mixture was again gradually warmed to -20 degrees
5. additionwas added
6. stirringAfter stirring for 18 hours at -20 degrees the reaction
7. customwas quenched with ice-cold 10% (v/v) hydrochloric acid
8. extractionthe organics were extracted into ethyl ether
9. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
10. customEvaporation of the
11. dry with materialdried (magnesium sulfate)
12. customextracts gave an oil which
13. customwas purified by flash chromatography on silica using 20% ethyl ether/hexanes