Trifluoroacetic acid → HCID 23442892, compound

Participants

Reaction Conditions

Reaction Steps

Under ice-cooling, 1.4 ml of trifluoroacetic acid was added dropwise to 0.25 g of 4-t-butyl-5-hydroxy-2-methylbenzofuran in 2.8 ml of triethylsilane. After stirring at 0° C. for 15 minutes and then at room temperature for 18 hours, the mixture was poured into ice water and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate) to give 0.18 g of 4-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a white crystal (yield 74%).

Provenance & Evidence