Tetrabutylammonium Fluoride → HCID 86761236, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3R)-1-(tert-butyl-dimethyl-silyloxy)-3-(3,4-dichloro-phenyl)-2-methanesulfonyloxy-butane (4.99 g, 11.7 mmol) in THF (117 mL) at 0° C. was added tetrabutylammonium fluoride (TBAF; 1.0 M in THF, 23.4 mL). The solution was stirred at 0° C. for 15 min, then was diluted with 1 N HCl (100 ml) and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to yield a yellow oil. The product was purified by flash chromatography (EtOAc/hexanes) to give 3.45 g (94%) of the desired product. 1H NMR (400 MHz, CDCl3): 7.41 (d, J=8.0, 1H), 7.35 (d, J=2.0, 1H), 7.12 (dd, J=8.2, 2.4, 1H), 4.82-4.78 (m, 1H), 3.88-3.84 (m, 1H), 3.74-3.69 (m, 1H), 3.17 (q, J=7.1, 1H), 2.78 (s, 3H), 1.98 (br s, 1H), 1.36 (d, J=7.2, 3H).

Provenance & Evidence