Sodium Hydroxide → (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid

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Reaction Steps

(Step 3) To methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate (190 mg, 0.52 mmol) obtained in Step 2, acetonitrile (10 mL) and an aqueous sodium hydroxide solution (0.5 mol/L, 5.2 mL, 2.58 mmol) were added, and the resulting mixture, was stirred at room temperature for 5.5 hours. To the reaction mixture, Dowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) was added thereto to neutralize the mixture, and the insoluble matter was removed by filtration, and then, the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, and then, the solvent was evaporated under reduced pressure, whereby (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid (156 mg) was obtained.

Provenance & Evidence