Acetic Acid → HCID 58742366, compound

Participants

Reaction Steps

To a solution of (2R,3S,4aR,10aR)-7-(tert-butyl-dimethylsilanyloxy)-4a-ethyl-2-(pyridin-3-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,3-diol (13 mg, 0.03 mmol) and acetic acid (0.05 mL, 0.87 mmol) in tetrahydrofuran (2 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.13 mL, 0.13 mmol). The mixture was stirred overnight at room temperature and the concentrated under vacuum. The residue was taken up in ethyl acetate and filtered through a plug of silica gel. The title compound, a solid (4.2 mg, 43%) was obtained by evaporation of the solvent. 1H NMR (CDCl3) selected signals: δ 9.00 (br s, 1 H), 8.50 (d, J=8.3 Hz, 1 H), 8.26 (d, J=5.7 Hz, 1 H), 7.32 (dd, J=5.7, 7.8 Hz, 1 H), 6.94 (d, J=8.3 Hz, 1 H), 6.65 (dd, J=2.6, 8.3 Hz, 1 H), 6.60 (d, J=2.6 Hz, 1 H), 4.23 (dd, J=4.7, 13.0 Hz, 1 H). MS: m/e 340 (M+1).

Provenance & Evidence