Ammonium Chloride → methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate

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Reaction Steps

(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,

Provenance & Evidence