tert-Butanol → tert-butyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate

Participants

Reaction Steps

(Step 4) To N,N′-diisopropylcarbodiimide (0.643 mL, 4.13 mmol), tert-butanol (0.415 mL, 4.34 mmol) and copper(I) chloride (20 mg, 0.21 mmol) were added, and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered, through Celite (registered trademark), and the solvent in the filtrate was evaporated under reduced pressure. To the obtained residue, dichloromethane (7.4 mL) and (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid (183 mg, 0.516 mmol) obtained in Step 3 were added, and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered through Celite (registered trademark), and the solvent of the filtrate was evaporated under reduced pressure. The resulting residue was purified by thin-layer chromatography (ethyl acetate/n-hexane=1/20), whereby tert-butyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate (40 mg, 19%) was obtained.

Provenance & Evidence