Cesium fluoride → (E)-3-cyclohexyl-2-(3-methanesulfonyl-phenyl)-prop-2-en-1-ol

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Reaction Steps

According to the procedure described for example 26b the use of 1-bromo-3-methanesulfonyl-benzene (1.07 g, 4.55 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.57 g, 5.92 mmol), caesium fluoride (2.07 g, 13.7 mmol) and tetrakis(triphenylphosphino)palladium(0) (525 mg, 455 μmol) in 40 mL dioxane with heating to reflux for 16 h gives a brown oil. Purify the crude product by column chromatography, eluting with a gradient from 100:0 to 0:100 hexanes:ethyl acetate to obtain (E)-3-cyclohexyl-2-(3-methanesulfonyl-phenyl)-prop-2-en-1-ol (693 mg) as a brown oil. MS (m/e): 277 [(M−H2O)+H].

Provenance & Evidence