반응 #1862951

반응 방정식

ammonium chloride

methyl (S)-2-(tert-butyldimethylsiloxy)-4-hydroxybutanoate

diisopropylethylamine

{(chloromethoxy)methyl}benzene

→

methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate

수율 59.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   추출the resulting mixture was extracted with ethyl acetate
2. 2
   건조The organic layer was dried over sodium sulfate
3. 3
   기타the solvent was evaporated under reduced pressure
4. 4
   기타The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=20/80)

실험 절차

(Step 2) To methyl (S)-2-(tert-butyldimethylsiloxy)-4-hydroxybutanoate (220 mg, 0.886 mmol) obtained in Step 1, dichloromethane (0.89 mL), diisopropylethylamine (0.464 mL, 2.66 mmol), and {(chloromethoxy)methyl}benzene (0.30 mL, 2.21 mmol) were added, and the resulting mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=20/80), whereby methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate (191 mg, 59%) was obtained,

출처