反应详情

To a solution of 5,5-dimethyl-3-prop-2-ynyl-3-trifluoromethyl-1,3,4,5-tetrahydrobenzo[c]oxepin-1-ol (2.50 g, 8.38 mmol) in tert-BuOH (75 mL) was added a 2.0 M solution of 2-methyl-2-butene in THF (58 mL, 117 mmol). To this solution was added a solution of sodium chlorite (4.74 g, 42.0 mmol) and sodium hydrogen phosphate (11.57 g, 84.0 mmol) in water (37.5 mL). The reaction mixture was stirred for 6 hours then the volatiles were removed in vacuo. The aqueous mixture was then acidified to pH=1 with aqueous 1M HCl, extracted with 300 mL of ethyl acetate, dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude was purified by flash chromatography (120 g SiO2, hexanes to 1:1 hexanes:EtOAc) to give 2-(3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid (2.30 g, 87%). MS (ES+) m/z 315 [M+H]+.

1. customthe volatiles were removed in vacuo
2. extractionextracted with 300 mL of ethyl acetate
3. dry with materialdried with magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude was purified by flash chromatography (120 g SiO2, hexanes to 1:1 hexanes:EtOAc)