prop-2-enylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a mixture of 3-cyclohexyl-1-propene (10 g), acetone (600 mL), water (140 mL) and acetic acid (13.5 mL) at RT was added a solution of potassium permanganate (22.3 g) in water (85 mL), followed by additional acetone (270 mL). After stirring for 40 min, sodium nitrite (11.7 g) was added, followed by dilute sulfuric acid (12%, 221 mL). The product was extracted with ether-hexanes (1:1), and the extracts were washed with saturated sodium bicarbonate and brine, dried (sodium sulfate) and concentrated. The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes to give the title compound. The product was extracted with ether-hexanes (1:1) the extracts were washed with saturated sodium bicarbonate and brine dried (sodium sulfate) concentrated The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes

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

Procedure: Toluene (5 mL) was added to 4-bromo-2-fluoroaniline (950 mg, 5.00 mmol), allylcyclohexane (1.15 mL, 7.50 mmol), palladium acetate (112 mg, 0.50 mmol), tris(2-methylphenyl)phosphine (457 mg, 1.50 mmol) and triethylamine (2.09 mL, 15.0 mmol), and the mixture was stirred, followed by heating to reflux for 10 hr. After cooling, ethyl acetate was added thereto, the mixture was filtered through Celite (registered trademark), and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a pale yellow oil (805 mg). by heating to reflux for 10 hr After cooling the mixture was filtered through Celite (registered trademark) the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography (hexane only→hexane

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

Procedure: To a mixture of 3-cyclohexyl-1-propene (10 g), acetone (600 mL), water (140 mL) and acetic acid (13.5 mL) at RT was added a solution of potassium permanganate (22.3 g) in water (85 mL), followed by additional acetone (270 mL). After stirring for 40 min, sodium nitrite (11.7 g) was added, followed by dilute sulfuric acid (12%, 221 mL). The product was extracted with ether-hexanes (1:1), and the extracts were washed with saturated sodium bicarbonate and brine, dried (sodium sulfate) and concentrated. The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes to give the title compound. The product was extracted with ether-hexanes (1:1) the extracts were washed with saturated sodium bicarbonate and brine dried (sodium sulfate) concentrated The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To toluene 3.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g were added allylcyclohexane 0.17 mL, cesium carbonate 0.36 g, tetrabutylammonium bromide 53 mg and polymer-carried bis(acetato)triphenylphosphine palladium(II) 86 mg at room temperature, and it was stirred at 110° C. for 22 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate. After the reaction mixture was cooled to room temperature insoluble matter was filtrated ethyl acetate and 10% citric acid aqueous solution were added to it The organic layer was separated collected dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution the solvent was removed under reduced pressure

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

Procedure: To a mixture of 3-cyclohexyl-1-propene (10 g), acetone (600 mL), water (140 mL) and acetic acid (13.5 mL) at RT was added a solution of potassium permanganate (22.3 g) in water (85 mL), followed by additional acetone (270 mL). After stirring for 40 min, sodium nitrite (11.7 g) was added, followed by dilute sulfuric acid (12%, 221 mL). The product was extracted with ether-hexanes (1:1), and the extracts were washed with saturated sodium bicarbonate and brine, dried (sodium sulfate) and concentrated. The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes to give the title compound. The product was extracted with ether-hexanes (1:1) the extracts were washed with saturated sodium bicarbonate and brine dried (sodium sulfate) concentrated The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes

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

Procedure: Toluene (5 mL) was added to 4-bromo-2-fluoroaniline (950 mg, 5.00 mmol), allylcyclohexane (1.15 mL, 7.50 mmol), palladium acetate (112 mg, 0.50 mmol), tris(2-methylphenyl)phosphine (457 mg, 1.50 mmol) and triethylamine (2.09 mL, 15.0 mmol), and the mixture was stirred, followed by heating to reflux for 10 hr. After cooling, ethyl acetate was added thereto, the mixture was filtered through Celite (registered trademark), and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a pale yellow oil (805 mg). by heating to reflux for 10 hr After cooling the mixture was filtered through Celite (registered trademark) the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography (hexane only→hexane

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

Procedure: To a mixture of 3-cyclohexyl-1-propene (10 g), acetone (600 mL), water (140 mL) and acetic acid (13.5 mL) at RT was added a solution of potassium permanganate (22.3 g) in water (85 mL), followed by additional acetone (270 mL). After stirring for 40 min, sodium nitrite (11.7 g) was added, followed by dilute sulfuric acid (12%, 221 mL). The product was extracted with ether-hexanes (1:1), and the extracts were washed with saturated sodium bicarbonate and brine, dried (sodium sulfate) and concentrated. The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes to give the title compound. The product was extracted with ether-hexanes (1:1) the extracts were washed with saturated sodium bicarbonate and brine dried (sodium sulfate) concentrated The resulting residue was purified on silica gel column eluting with 5-100% ether in hexanes

Conditions: temp:0.00; pressure:0.00; stir: