Tetrabutylammonium Fluoride → HCID 86605360, compound

Participants

Reaction Steps

Compound 44 (22 g, 30.0 mmol) is dissolved in THF (200 L) and treated with TBAF (1M in THF, 30.68 mL) and the reaction mixture is stirred at room temperature for 2 h followed by concentration. The residue is purified on a silica gel column using chloroform:methanol (100:0 to 90:10) as an eluent to give 10g (70%) of 45 as a white foam, mp 188° C.: 1H NMR (DMSO-d6): δ: 8.23 (s, 1 H), 7.89 (s, 1 H), 7.4-6.9 (m, 14 H), 5.01 (bs, 1 H), 4.36 (m, 1 H), 3.84 (m, 1 H), 3.71 (s, 3 H), 3.67 (m, 1 H, partially masked by CH3 peak), 1.90 (m, 2 H), 0.73 (t, J=7.3 Hz, 3H). IR (KBr, cm−1) 3408, 3313, 2966, 1715, 1605, 1469 and 1249.

Provenance & Evidence