Tetrabutylammonium Fluoride → HCID 90412648, compound

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride 1M in THF (3 ml) was added to a solution of 13 (1.1 g, 1.45 mmol) in 10 ml of THF. The reaction was kept at room temperature for 2 days until no staring material was seen by HPLC analysis. The reaction was concentrated and partitioned between water and ethyl acetate. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The resulting material was chromatographed on silica eluting with a gradient of acetone (0-40%) in ethyl acetate. Concentration of the pure product fractions afforded 0.9 g (96%) of 14 as a white amorphous solid. 1H NMR (DMSO-d6): δ 11.12 (s, 1H), 8.70 (s, 1H), 8.34 (s, 1H), 8.05 (d, J=8.7 Hz, 2H), 7.65 (m, 1H), 7.56 (t, J=7.5 Hz, 2H), 7.18 (m, 5H), 7.04 (m, 4H), 6.77 (m, 4H), 4.79 (d, J=4.8 Hz, 1H), 4.39 (m, 2H), 3.80 (m, 1H), 3.71 (s, 6H), 3.09 (m, 1H), 2.88 (m, 1H), 2.31 (m, 1H), 1.03 (d, J=6.3 Hz, 3H).

Provenance & Evidence