反应详情

Lithium aluminum hydride (a 1M solution in tetrahydrofuran; 1.1 ml, 1.1 mmol) was added dropwise to a solution of 3-(1-azidotridecyl)-5-trimethylsilylfuran (334 mg, 0.92 mmol) in tetrahydrofuran at room temperature. After one hour at room temperature, the excess hydride was destroyed by adding acetone slowly to the mixture with cooling. Sodium sulfate (ca. 0.5 g) was added and the mixture was extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 5% methanol/dichloromethane containing 0.2% triethylamine. Fractions with Rf of about 0.18 on evaporation gave the title amine as a pale yellow oil.

1. customthe excess hydride was destroyed
2. additionby adding acetone slowly to the mixture
3. temperaturewith cooling
4. additionSodium sulfate (ca. 0.5 g) was added
5. extractionthe mixture was extracted thoroughly with ethyl acetate
6. customEvaporation of the
7. dry with materialdried (magnesium sulfate)
8. customextracts gave an oil, which
9. customwas purified by flash chromatography on silica using 5% methanol/dichloromethane containing 0.2% triethylamine
10. customFractions with Rf of about 0.18 on evaporation