Tetrabutylammonium Fluoride → [6-[[2-Chloro-5-(trifluoromethyl)phenoxy]methyl]dithiin-3-yl]methanol

Participants

Reaction Steps

To a stirred solution of the 3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-chloro-5-trifluoromethyl-phenyloxy)methyl]-1,2-dithiin obtained above (290 mg, 0.62 mmol) in 8 mL of THF was added a solution of 4 mL of 1M tetrabutylammonium fluoride in THF and 2.5 mL of acetic acid. The reaction mixture was stirred for 5 h until TLC analysis showed the reaction to be complete. The reaction mixture was partitioned between 30 mL of water and 50 mL of ethyl acetate. The organic phase was washed with 3% aqueous sodium bicarbonate (50 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and then the combined organic layer was washed with water, dried over magnesium sulfate and concentrated to a small volume. The residue was chromatographed over a silica gel column (ethyl acetate-hexane, 1:3) to yield 120 mg (57%) of the title compound as a yellow solid. The compound was further purified by reverse phase HPLC (PRP-1 column, acetonitrile:water gradient), mp 94.2°-96° C.; 1H NMR (CDCl3):δ7.51 (d, J=8.4, 1 H), 7.22 (dd, J=6.8, J=2.0, 1 H), 7.16 (d, J=l.2, 1 H), 6.55 (d, J=6.0, 1 H), 6.5 (d, J=6.0, 1 H), 4.79 (s, 2 H), 4.31 (d, 2 H, J=5.6) 1.80 (t, J=6.0, 1 H); 13C NMR(CDCl3):δ153.69, 136.86, 136.49, 130.98, 130.85, 128.30, 127.54, 124.77, 119.13, 118.28, 111.03, 70.73, 64.53, MS (EI):354 (M+). Anal. calcd for C13H10ClF3O2S2 :C, 44.01; H, 2.84. Found:C, 43.74; H, 2.94.

Provenance & Evidence