Methanol → 2-((5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)thio)-5-thiazolecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.183 g (0.47 mmol) of ethyl 2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthylthio)-5-thiazolecarboxylate (Compound 14) in 2.0 mL of THF was added 1.0 mL of LiOH (2.1N aqueous solution) and 1.0 mL of MeOH. The solution was heated at 50° C. for 1 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with water, the aqueous layer acidified to pH=1 using 10% HCl and extracted with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered, and the solvents removed in vacuo to give the title compound as a white solid (131 mg, 78%): PNMR (300 MHz, CD3OD) δ 1.28 (s, 6H), 1.32 (s, 6H), 1.73 (s, 4H), 2.40 (s, 3H), 7.42 (s, 1H), 7.63 (s, 1H), 8.12 (s, 1H).

Provenance & Evidence