Tetrabutylammonium Fluoride → (+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethanol

Participants

Reaction Steps

Treatment of (±)-tert-butyl(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethoxy)dimethylsilane (4.38 g; 0.014 mol) with tetrabutylammonium fluoride (16.5 mL, 1.0 M solution in tetrahydrofuran) generally according to the procedure described for Intermediate 6 afforded 1.9 g (67%) of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethanol as a colorless oil. Rf=0.12 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C13H16O2.0.1H2O: C, 75.77; H, 7.92. Found: C, 75.77; H, 7.93.

Provenance & Evidence