Iodoethane → HCID 178440102, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 200 mg (0.36 mmol) of trans 2,4-dimethyl-thiazole-5-sulfonic acid [4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide in 5 mL of THF was cooled to −78° C. and treated dropwise with 0.25 mL of a 1.6 M solution of nBuLi in hexane. The solution was warmed to −30° C., treated with 1 mL (1.2 mmol) of ethyliodide, allowed to reach RT and then refluxed for 2 hrs. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave a residue that was redissolved in THF and treated with an excess of TBAF. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation of the solvent and chromatography on silicagel with heptane/EtOAc 2:1 yielded 20 mg (11%) of trans 4-methyl-2-propyl-thiazole-5-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide as a yellow oil, MS: 497 (M+H)+.

Provenance & Evidence