2-Methyl-2-butene → HCID 58026119, compound

Participants

Reaction Steps

To a solution of 15 g (0.031 mol) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzaldehyde in 240 mL of tert-BuOH was added a solution of the 62 mL (0.124 mol) of 2-methyl-2-butene in THF (2 M). To this solution was added a solution of the 17.5 g of sodium chlorite (0.150 mol) and 42.8 g of sodium hydrogen phosphate (0.138 mol) in water. The reaction mixture was stirred overnight. The volatiles were removed in vacuo. The aqueous mixture was then acidified to pH=1 with 1 M HCl, extracted with 1200 mL of ethyl acetate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 10-100% ethyl acetate/hexanes to afford 10.6 g (103%) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid.

Provenance & Evidence