(4-甲基-1-双环[2.2.2]辛基)甲醇

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.156 Mole of p-toluenesulfonyl chloride is dissolved in 150 ml. of anhydrous pyridine at 0° C, under nitrogen, and then 0.078 mole of 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane is added slowly and the mixture then stirred for two hours. 2 Ml. of water is then added and the mixture stirred for five minutes and then poured into 600 ml. of ethyl acetate. The organic phase is washed twice with water, then washed with 2 Normal aqueous hydrochloric acid until no more pyridine remains. The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate is then evaporated under vacuum affording 4-methylbicyclo[2.2.2]oct-1-yl methanol tosylate. the mixture stirred for five minutes poured into 600 ml The organic phase is washed twice with water washed with 2 Normal aqueous hydrochloric acid until no more pyridine The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution dried over anhydrous magnesium sulfate filtered The filtrate is then evaporated under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.156 Mole of p-toluenesulfonyl chloride is dissolved in 150 ml. of anhydrous pyridine at 0° C, under nitrogen, and then 0.078 mole of 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane is added slowly and the mixture then stirred for two hours. 2 Ml. of water is then added and the mixture stirred for five minutes and then poured into 600 ml. of ethyl acetate. The organic phase is washed twice with water, then washed with 2 Normal aqueous hydrochloric acid until no more pyridine remains. The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate is then evaporated under vacuum affording 4-methylbicyclo[2.2.2]oct-1-yl methanol tosylate. the mixture stirred for five minutes poured into 600 ml The organic phase is washed twice with water washed with 2 Normal aqueous hydrochloric acid until no more pyridine The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution dried over anhydrous magnesium sulfate filtered The filtrate is then evaporated under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.0952 Mole of lithium aluminum hydride is dissolved in 200 ml. of anhydrous diethyl ether, under nitrogen, and cooled to 0° C. 0.0952 Mole of 4-methylbicyclo[2.2.2]oct-1-yl carboxylic acid in 100 ml. of tetrahydrofuran is added dropwise, then the mixture stirred for 30 minutes. Excess lithium aluminum hydride is decomposed by the cautious addition of ethyl acetate, followed by the careful addition of 10 ml. of water. The mixture is then filtered and the filtrate washed with ethyl ether, then dried over anhydrous magnesium sulfate and filtered. The solvent is then evaporated from the filtrate, under vacuum, affording 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane. followed by the careful addition of 10 ml The mixture is then filtered the filtrate washed with ethyl ether dried over anhydrous magnesium sulfate filtered The solvent is then evaporated from the filtrate, under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.156 Mole of p-toluenesulfonyl chloride is dissolved in 150 ml. of anhydrous pyridine at 0° C, under nitrogen, and then 0.078 mole of 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane is added slowly and the mixture then stirred for two hours. 2 Ml. of water is then added and the mixture stirred for five minutes and then poured into 600 ml. of ethyl acetate. The organic phase is washed twice with water, then washed with 2 Normal aqueous hydrochloric acid until no more pyridine remains. The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate is then evaporated under vacuum affording 4-methylbicyclo[2.2.2]oct-1-yl methanol tosylate. the mixture stirred for five minutes poured into 600 ml The organic phase is washed twice with water washed with 2 Normal aqueous hydrochloric acid until no more pyridine The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution dried over anhydrous magnesium sulfate filtered The filtrate is then evaporated under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 0.0952 Mole of lithium aluminum hydride is dissolved in 200 ml. of anhydrous diethyl ether, under nitrogen, and cooled to 0° C. 0.0952 Mole of 4-methylbicyclo[2.2.2]oct-1-yl carboxylic acid in 100 ml. of tetrahydrofuran is added dropwise, then the mixture stirred for 30 minutes. Excess lithium aluminum hydride is decomposed by the cautious addition of ethyl acetate, followed by the careful addition of 10 ml. of water. The mixture is then filtered and the filtrate washed with ethyl ether, then dried over anhydrous magnesium sulfate and filtered. The solvent is then evaporated from the filtrate, under vacuum, affording 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane. followed by the careful addition of 10 ml The mixture is then filtered the filtrate washed with ethyl ether dried over anhydrous magnesium sulfate filtered The solvent is then evaporated from the filtrate, under vacuum