2-Methyl-3-butyn-2-ol → HCID 66582304, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL vial was charged with 2-(3′-chloro-4′-(phenylsulfonyl)-4-biphenylyl)-1,1,1-trifluoro-2-propanol (0.300 g, 0.680 mmol, Example 19), 2-methyl-3-butyn-2-ol (0.099 mL, 1.021 mmol, Sigma-Aldrich, St. Louis, Mo.), potassium carbonate (0.235 g, 1.701 mmol), 2 mL of dimethylacetamide, 2-(dicyclohexylphosphino)-2′,4′,6′,-triisopropyl-biphenyl (XPhos) (9.73 mg, 0.020 mmol, Strem Chemical Inc, Newburyport, Mass.), and tris(dibenzylideneacetone)dipalladium (0) (0.021 g, 0.020 mmol, Strem Chemical Inc, Newburyport, Mass.). The vial was sealed and heated at 100° C. for 2 h. After that time, the mixture was concentrated and purified by column chromatography (40 g of silica, 0 to 40% EtOAc in hexane) to give 2-methyl-4-(4-(phenylsulfonyl)-4′-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-3-biphenylyl)-3-butyn-2-ol (0.035 g) as a mixture of two enantiomers.

Provenance & Evidence