2-(4-ethynylphenyl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A flask is flushed with N2 and charged with 4-bromo-phenethyl alcohol (20 mmol) and dissolved in 1/1 Et3N/dioxane. Bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) (0.2 mmol) is added, followed by 0.4 mmol of CuI. Trimethylsilylacetylene (24 mmol) is added drop-wise to the reaction mixture. The reaction mixture is stirred overnight under N2. The solvent is removed under vacuum and the resulting liquid is extracted by washing with ethyl ether. The ethyl ether extracts are combined and washed with H2O, then dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the product is purified by column chromatography. The purified product is placed in a N2-flushed flask and dissolved in methanol. Potassium fluoride (65 mmol) is added and the reaction stirred under a N2 blanket for 16 h. The reaction mixture is poured into CH2Cl2 and extracted with H2O, then dried over Na2SO4, filtered and the solvent is removed under vacuum. The resulting product is purified by column chromatography to yield 2-(4-ethynyl-phenyl)-ethanol (2). A flask is flushed with N2 The solvent is removed under vacuum the resulting liquid is extracted by washing with ethyl ether washed with H2O dried over anhydrous sodium sulfate The solvent is removed under vacuum the product is purified by column chromatography flushed flask dissolved in methanol the reaction stirred under a N2 blanket for 16 h extracted with H2O dried over Na2SO4 filtered the solvent is removed under vacuum The resulting product is purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A flask is flushed with N2 and charged with 4-bromo-phenethyl alcohol (20 mmol) and dissolved in 1/1 Et3N/dioxane. Bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) (0.2 mmol) is added, followed by 0.4 mmol of CuI. Trimethylsilylacetylene (24 mmol) is added drop-wise to the reaction mixture. The reaction mixture is stirred overnight under N2. The solvent is removed under vacuum and the resulting liquid is extracted by washing with ethyl ether. The ethyl ether extracts are combined and washed with H2O, then dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the product is purified by column chromatography. The purified product is placed in a N2-flushed flask and dissolved in methanol. Potassium fluoride (65 mmol) is added and the reaction stirred under a N2 blanket for 16 h. The reaction mixture is poured into CH2Cl2 and extracted with H2O, then dried over Na2SO4, filtered and the solvent is removed under vacuum. The resulting product is purified by column chromatography to yield 2-(4-ethynyl-phenyl)-ethanol (2). A flask is flushed with N2 The solvent is removed under vacuum the resulting liquid is extracted by washing with ethyl ether washed with H2O dried over anhydrous sodium sulfate The solvent is removed under vacuum the product is purified by column chromatography flushed flask dissolved in methanol the reaction stirred under a N2 blanket for 16 h extracted with H2O dried over Na2SO4 filtered the solvent is removed under vacuum The resulting product is purified by column chromatography