Sodium Hydroxide → HCID 178525777, compound

Participants

Reaction Steps

To a solution of cis/trans-4-[1-hydroxymethyl-2-(toluene-4-sulfonyloxy)-ethoxy]-cyclohexanecarboxylic acid ethyl ester (3:7) (0.46 g, 1.2 mmol) in toluene (11.5 ml) was added potassium tert-butoxide (0.14 g, 1.3 mmol). The reaction mixture was heated at reflux for 20 h. After cooling to room temperature the mixture was partitioned between ethyl acetate (50 ml) and 1 M aqueous hydrogen chloride solution (30 ml). The layers were separated. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in 1,4-dioxane (12 ml) and 2 M aqueous sodium hydroxide solution (5.7 ml, 12 mmol). After stirring at room temperature for 16 h the mixture was partitioned between tert-butyl methyl ether (30 ml) and 1 M aqueous sodium hydroxide solution (50 ml). The layers were separated. The organic layer was extracted with one 50-ml portion of 1 M aqueous sodium hydroxide solution. The combined aqueous layers were acidified by addition of concentrated hydrochloric acid solution and crushed ice (50 g) and extracted with three 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.12 g, 50%) as off-white solid. MS m/e: 199 (M+H+)

Provenance & Evidence