3-prop-2-ynoxyprop-1-yne

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 168.12 g. (0.5 mole) of hexafluorobisphenol A in 1000 ml of acetone was reacted with 142.76 g. (1.2 moles) of propargyl bromide in the presence of 165.85 g. (1.2 moles) of potassium carbonate. The reaction mixture was stirred and heated under reflux for 72 hrs. After cooling it was filtered and the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor. The residue was dissolved in diethyl ether and washed first with a 5% NaOH solution and then three times with deionized water. Dipropargyl ether of hexafluorobisphenol A was obtained in 90% yield after evaporation of diethyl ether on a Rotavapor. The product was a light brown liquid with the following structure. ##STR11## heated under reflux for 72 hrs After cooling it was filtered the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor The residue was dissolved in diethyl ether washed first with a 5% NaOH solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 168.12 g. (0.5 mole) of hexafluorobisphenol A in 1000 ml of acetone was reacted with 142.76 g. (1.2 moles) of propargyl bromide in the presence of 165.85 g. (1.2 moles) of potassium carbonate. The reaction mixture was stirred and heated under reflux for 72 hrs. After cooling it was filtered and the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor. The residue was dissolved in diethyl ether and washed first with a 5% NaOH solution and then three times with deionized water. Dipropargyl ether of hexafluorobisphenol A was obtained in 90% yield after evaporation of diethyl ether on a Rotavapor. The product was a light brown liquid with the following structure. ##STR11## heated under reflux for 72 hrs After cooling it was filtered the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor The residue was dissolved in diethyl ether washed first with a 5% NaOH solution

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a round bottom flask with reflux condenser were placed 1.0 g of 3-Prop-2-ynyloxy-propyne and 2.08 g of propargylic alcohol in 10 ml ethanol, followed by the addition of 9.8 mg of tris(triphenylphosphine)rhodium chloride (Wilkinson catalyst) at room temperature. The reaction was heated up to 70° C., while the reaction colour turned yellow rapidly. After 1 day stirring at r.t., TLC analysis showed complete conversion of the starting material. The solvent was evaporated, diluted with DCM and extracted with H2O, dried over MgSO4. The brown mixture was purified by flash chromatography using 8/2 cyclohexane/AcOEt as mobile phase affording (1,3-Dihydro-isobenzofuran-5-yl)-methanol as a colourless pure solid (0.92 g, 60%). In a round bottom flask with reflux condenser The solvent was evaporated diluted with DCM extracted with H2O dried over MgSO4 The brown mixture was purified by flash chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7 g (19.9 mmol) of 8-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to boiling under reflux for 3 hours with 2.5 ml (29 mmol) of propargyl ether, 100 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 30 mg of copper(I) iodide in 70 ml of diethylamine. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. After recrystallization from ethyl acetate there was obtained 8-fluoro-4,5-dihydro-3-(3-methoxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 146°-147°. The reaction mixture was evaporated the residue was chromatographed on silica gel while eluting with ethyl acetate After recrystallization from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 168.12 g. (0.5 mole) of hexafluorobisphenol A in 1000 ml of acetone was reacted with 142.76 g. (1.2 moles) of propargyl bromide in the presence of 165.85 g. (1.2 moles) of potassium carbonate. The reaction mixture was stirred and heated under reflux for 72 hrs. After cooling it was filtered and the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor. The residue was dissolved in diethyl ether and washed first with a 5% NaOH solution and then three times with deionized water. Dipropargyl ether of hexafluorobisphenol A was obtained in 90% yield after evaporation of diethyl ether on a Rotavapor. The product was a light brown liquid with the following structure. ##STR11## heated under reflux for 72 hrs After cooling it was filtered the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor The residue was dissolved in diethyl ether washed first with a 5% NaOH solution