Tetrabutylammonium Fluoride → [3-(Tetrahydro-pyran-2-yloxy)-cyclobutyl]-methanol

Participants

Reaction Steps

tert-Butyl dimethyl-[3-(tetrahydropyran-2-yloxy)-cyclobutylmethoxy]-silane (1.62 g) was dissolved in tetrahydrofuran (11 mL) and treated with a solution of 1.0M tetrabutylammonium fluoride in tetrahydrofuran (8.08 mL) for 2 hours. The reaction mixture was diluted with dichloromethane and the mixture was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 2:3 by volume) to give the title compound (0.84 g). 1H NMR (300 MHz, CHCl3-d): δ 4.62-4.54 (m, 1H), 4.29-4.20 (m, 1H), 3.88 (d, 1H), 3.68-3.60 (m, 2H), 3.53-3.42 (m, 1H), 2.30-2.20 (m, 2H), 2.19-2.08 (m, 2H), 1.86-1.72 (m, 3H), 1.58-1.47 (m, 4H), 1.34 (s, 1H).

Provenance & Evidence