Lithium Hydroxide → HCID 58227488, compound

Participants

Reaction Steps

A solution of 2-phenylethynyl-thiazole-5-carboxylic acid ethyl ester (9.00 g, 35.0 mmol), lithium hydroxide (13.5 g, 563 mmol), tetrahydrofuran (190 mL) and water (143 mL) was stirred at 25° C. for 64 h. The material was concentrated to remove most of the THF, taken up in 350 mL of water and washed with EtOAc (3×50 mL); acidified with 3.7% HCl to pH<1 and the precipitate extracted with 3×100 mL of EtOAc. The combined EtOAc extracts were washed with 50 mL of water, 50 mL of brine, dried (Na2SO4) and concentrated to give the titled compound, 2-phenylethynyl-thiazole-5-carboxylic acid (7.79 g; 97%), as a yellow powder, which was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 1H), 7.69-7.60 (m, 2H), 7.51-7.38 (m, 3H). LC/MS (Method 1), RT=0.57 min. Calculated [M+H]+=230; Observed [M+H]+=230.

Provenance & Evidence