Water → 5-Isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran

Participants

Reaction Conditions

Reaction Steps

To a cold solution (0° C.) of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol (1.97 g, 8.93 mmol) in dry dichloromethane (40 mL) was added triethylsilane (2.85 mL, 17.86 mmol). After 10 minutes, trifluoroacetic acid was added and the reaction mixture stirred at 0° C. for 30 minutes. Water was poured into the reaction mixture and the layers separated. The organic layer was further washed with water, aqueous NaHCO3 and brine, dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (0% to 5% ethyl acetate in hexane) to give 1.6 g of 5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran (87%). 1H NMR (300 MHz; CDCl3): δ 0.90 (d, J=6.3 Hz, 6H), 1.32 (s, 6H), 1.79 (m, 1H), 2.40 (d, J=6.9 Hz, 2H), 4.20 (s, 2H), 6.68 (dd, J=1.2 Hz and 7.5 Hz, 1H), 6.87 (m, 2H).

Provenance & Evidence