(2,3,4,5,6-pentafluorophenyl) thiohypochlorite

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

Procedure: Under agitation and using argon as the protective gas, 15 ml of about 1.6N n-butyllithium in hexane, diluted with 30 ml of toluene, is added dropwise at -5° to 0° to a solution of 8.83 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole in a mixture of 75 ml of absolute tetrahydrofuran and 75 ml of toluene. After 20 minutes, the pentafluorophenylsulfenyl chloride solution is added dropwise to the reaction mixture, maintaining the temperature between -5° and 0° by cooling. After 2 hours' stirring at room temperature, the solution is diluted with 200 ml of ethyl acetate, washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is purified by chromatography on aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane yields 8.86 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)-2-(pentafluorophenylthio)imidazole, mp 156°-158°. maintaining the temperature between -5° and 0° by cooling washed with sodium bicarbonate solution the organic solution is dried over sodium sulfate concentrated to dryness under vacuum The residue is purified by chromatography on aluminum oxide Recrystallization from ethyl acetate/hexane

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

Procedure: Under agitation and using argon as the protective gas, 15 ml of about 1.6N n-butyllithium in hexane, diluted with 30 ml of toluene, is added dropwise at -5° to 0° to a solution of 8.83 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole in a mixture of 75 ml of absolute tetrahydrofuran and 75 ml of toluene. After 20 minutes, the pentafluorophenylsulfenyl chloride solution is added dropwise to the reaction mixture, maintaining the temperature between -5° and 0° by cooling. After 2 hours' stirring at room temperature, the solution is diluted with 200 ml of ethyl acetate, washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is purified by chromatography on aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane yields 8.86 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)-2-(pentafluorophenylthio)imidazole, mp 156°-158°. maintaining the temperature between -5° and 0° by cooling washed with sodium bicarbonate solution the organic solution is dried over sodium sulfate concentrated to dryness under vacuum The residue is purified by chromatography on aluminum oxide Recrystallization from ethyl acetate/hexane

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

Procedure: Under agitation and using argon as the protective gas, 15 ml of about 1.6N n-butyllithium in hexane, diluted with 30 ml of toluene, is added dropwise at -5° to 0° to a solution of 8.83 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole in a mixture of 75 ml of absolute tetrahydrofuran and 75 ml of toluene. After 20 minutes, the pentafluorophenylsulfenyl chloride solution is added dropwise to the reaction mixture, maintaining the temperature between -5° and 0° by cooling. After 2 hours' stirring at room temperature, the solution is diluted with 200 ml of ethyl acetate, washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is purified by chromatography on aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane yields 8.86 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)-2-(pentafluorophenylthio)imidazole, mp 156°-158°. maintaining the temperature between -5° and 0° by cooling washed with sodium bicarbonate solution the organic solution is dried over sodium sulfate concentrated to dryness under vacuum The residue is purified by chromatography on aluminum oxide Recrystallization from ethyl acetate/hexane

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

Procedure: Under agitation and using argon as the protective gas, 15 ml of about 1.6 N n-butyllithium in hexane, diluted with 30 ml of toluene, is added dropwise at -5° to 0° to a solution of 8.83 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole in a mixture of 75 ml of absolute tetrahydrofuran and 75 ml of toluene. After 20 minutes, the pentafluorophenylsulfenyl chloride solution is added dropwise to the reaction mixture, maintaining the temperature between -5° and 0° by cooling. After 2 hours' stirring at room temperature, the solution is diluted with 200 ml of ethyl acetate, washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is purified by chromatography on aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane yields 8.86 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)-2-(pentafluorophenylthio)imidazole, mp 156°-158°. maintaining the temperature between -5° and 0° by cooling washed with sodium bicarbonate solution the organic solution is dried over sodium sulfate concentrated to dryness under vacuum The residue is purified by chromatography on aluminum oxide Recrystallization from ethyl acetate/hexane

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

Procedure: Under agitation and using argon as the protective gas, 15 ml of about 1.6N n-butyllithium in hexane, diluted with 30 ml of toluene, is added dropwise at -5° to 0° to a solution of 8.83 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole in a mixture of 75 ml of absolute tetrahydrofuran and 75 ml of toluene. After 20 minutes, the pentafluorophenylsulfenyl chloride solution is added dropwise to the reaction mixture, maintaining the temperature between -5° and 0° by cooling. After 2 hours' stirring at room temperature, the solution is diluted with 200 ml of ethyl acetate, washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is purified by chromatography on aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane yields 8.86 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)-2-(pentafluorophenylthio)imidazole, mp 156°-158°. maintaining the temperature between -5° and 0° by cooling washed with sodium bicarbonate solution the organic solution is dried over sodium sulfate concentrated to dryness under vacuum The residue is purified by chromatography on aluminum oxide Recrystallization from ethyl acetate/hexane