Trifluoroacetic acid → 4-Tert-butyl-5-hydroxy-2-octyl-2,3-dihydrobenzofuran

Participants

Reaction Conditions

Reaction Steps

2.8 ml of triethylsilane was added to 0.3 g of 4-t-butyl-5-hydroxy-2-n-octylbenzofuran and then 1.4 ml of trifluoroacetic acid was added dropwise to this mixture under ice-cooling. After stirring at 0° C. for 15 minutes and then at room temperature for 1 hour, 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 chloroform) to give 0.25 g of 4-t-butyl-5-hydroxy-2-n-octyl-2,3-dihydrobenzofuran as a colorless oil (yield 83%).

Provenance & Evidence