Tetrabutylammonium Fluoride → HCID 15050935, compound

Participants

Reaction Steps

Compound l , 15 (15 mg, 0.03 mmol) was dissolved in 1 mL CHCl3, and a solution of 1M tetrabutylammonium fluoride in THF (40 μl) was added. The solution was allowed to stand at room temperature overnight. The solvent was removed in vacuo, and the remaining residue was dissolved in saturated NaHCO washed with ether to remove non-polar impurities, and extracted with CHCl3. The CHCl3 extracts were combined, evaporated, and purified on a short silica gel column to yield 10 mg (86%) of 16 as a waxy solid: 1H NMR (CDCl3) δ 2.05-2.50 (m, 60 H), 2.20 (s, 3 H, CH3), 3.22 (d, J=14 Hz, 1 H), 3.60 (m, 1 H), 4.80 (s, 2 H, CH20), 7.30 (dd, J=7.8, 4.7 Hz, 1 H), 7.44 (d, J=8.1 Hz, 1 H), 7.50 (dd, J=1.6, 7.8 Hz, 1 H), 7.62 (s, 1 H), 7.96 (d, J=8.1 Hz, 1 H), 8.02 (m, 1 H); MS (CI/NH3) m/e 382 (MH+, base), 242, 141, 113.

Provenance & Evidence