Lithium hydroxide, monohydrate → HCID 71712073, compound

Participants

Reaction Steps

Lithium hydroxide monohydrate (0.022 g, 0.52 mmol) was added to a stirred solution of {4-[4-(3-chloro-benzenesulfonyl)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.063 g, 0.12 mmol) in a 3:1 THF—H2O mixture (4 mL). The reaction mixture was stirred for 16 hours at room temperature. The THF was distilled off under reduced pressure, and the crude residue was diluted with water, acidified [pH˜2] via the drop-wise addition of an aqueous solution of hydrochloric acid (6.0 N). The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Trituration with hexanes afforded {4-[4-(3-chloro-benzenesulfonyl)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (0.031 g, 51%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.47 (br. s, 1 H) 8.19 (d, J=8.20 Hz, 2 H) 8.13 (t, J=2.10 Hz, 1 H) 8.05 (d, J=7.60 Hz, 1 H) 8.00 (dd, J=8.90, 5.80 Hz, 1 H) 7.91 (s, 1 H) 7.84 (d, J=7.60 Hz, 1 H) 7.72 (t, J=8.10 Hz, 1 H) 7.54 (d, J=8.10 Hz, 2 H) 7.38 (td, J=8.30, 2.60 Hz, 1 H) 6.64 (dd, J=10.90, 2.40 Hz, 1 H) 3.84 (s, 2 H) 2.03 (s, 3 H). MS calcd. for C25H18ClFO4S [(M−H)−] 467, obsd. 467.3.

Provenance & Evidence