Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate → methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate

Participants

Reaction Steps

Methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate (1000 mg, 2.33 mmol) was dissolved in methanol (30 mL) and 10% palladium on charcoal (100 mg) added. The mixture was stirred at ambient temperature for 36 h, filtered, evaporated in vacuo and chromatographed, 0-100% ethyl acetate in isohexane, to give methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate (750 mg). The material was used without further purification.

Provenance & Evidence