Tetrabutylammonium Fluoride → HCID 86605354, compound

Participants

Reaction Steps

A solution of 15 (10.6 g, 12.02 mmol) in THF (120 mL) is treated with tetrabutyl ammonium fluoride (1M in THF, 12.1 mL) and the reaction mixture stirred at room temperature for 2 h followed by concentration. The residue is purified on a silica gel column using ethyl acetate:hexanes:methanol (1:1:0 to 1:1:0.1) to give 8.87 g (96%) of 16 as a white solid: 1H NMR (DMSO-d6): δ 8.21 (s, 1H), 7.92 (s, 1H), 7.38-7.05 (m, 25H), 6.89 (d, J=9.1 Hz, 2H), 6.82 (d, J=9.0 Hz, 2H), 5.09 (t, J=5.4 Hz, 1H), 4.88-4.77 (m, 1H), 3.77-3.70 (m, 2H), 3.76 (s, 3H), 3.73 (s, 3H), 2.96-2.76 (m, 2H), 2.44-2.27 (m, 1H), 2.27-2.11 (m, 1H). IR (KBr, cm−1) 3412, 2932, 1734, 1606, 1509, 1251 and 1033. Anal. Calcd for C49H45N5O4.0.25 H2O.0.4 EtOAc: C, 75.25; H, 6.08; N, 8.67. Found: C, 75.35; H, 6.04; N, 8.50.

Provenance & Evidence