반응 #562716

반응 방정식

Dess-Martin reagent

3-methoxy-3-methyl-1-butanol

Hydroxyamine hydrochloride

3-methoxy-3-methylbutanal

→

N-hydroxy-3-methoxy-3-methylbutan-1-imine

수율 38.2%

용매

chloroform

Chloroform

pyridine

Ethyl acetate

반응 조건

후처리

1. 1
   세척the organic layer was washed with an aqueous solution of 20 wt. % sodium thiosulfate
2. 2
   건조The organic layer was dried over magnesium sulfate
3. 3
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
4. 4
   기타obtaining a crude product
5. 5
   기타obtained crude product (30 ml) under ice cooling
6. 6
   workup.STIRRINGstirred at room temperature overnight under nitrogen atmosphere
7. 7
   세척the organic layer was washed with water, 1M-hydrochloric acid aqueous solution and saturated brine
8. 8
   건조The organic layer was dried over magnesium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
10. 10
    기타The residue was purified by column chromatography (KP-Sil, Biotage, ethyl acetate/n-hexane=10 to 50%)

실험 절차

Dess-Martin reagent (15.0 g) was added to a chloroform solution (35 ml) of 3-methoxy-3-methyl-1-butanol (3.3 g) under ice cooling and stirred at room temperature for 5 hours. Chloroform was added to the reaction mixture and the organic layer was washed with an aqueous solution of 20 wt. % sodium thiosulfate, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure, thereby obtaining a crude product containing 3-methoxy-3-methylbutanal. Hydroxyamine hydrochloride (3.5 g) was added to a pyridine solution of the obtained crude product (30 ml) under ice cooling and stirred at room temperature overnight under nitrogen atmosphere. Ethyl acetate was added to the reaction mixture and the organic layer was washed with water, 1M-hydrochloric acid aqueous solution and saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (KP-Sil, Biotage, ethyl acetate/n-hexane=10 to 50%), thereby obtaining (N-hydroxy-3-methoxy-3-methylbutan-1-imine (1.4 g) as a colorless oily substance.

출처