1,3-diphenylpropan-2-ol

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: 258 mg (1 mmol) of (dibenzyl)acetyl chloride in 1 ml of toluene are added at room temperature to 140 mg (1.1 mmol) of N-hydroxypyridine-2-thione and 0.1 ml of pyridine in 5 ml of toluene. The mixture is maintained with stirring for 30 minutes. The filtered solution is added dropwise during 20 minutes to 1 ml of t-butylmercaptan in 20 ml of toluene at 80° C., and a vigorous stream of oxygen is passed into this solution. The reaction is continued for 1 hour at 80° C., and the reaction mixture is then stirred for 2 hours at room temperature before being poured into 10 ml of a saturated solution of potassium carbonate. The organic phase is again washed twice with potassium carbonate (2×10 ml), then with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate, filtered and evaporated to dryness. The crude product obtained is filtered on silica (100% CH2Cl2) to give 174 mg of the corresponding hydroxylated derivative. Yield 82%. The mixture is maintained The reaction is continued for 1 hour at 80° C. the reaction mixture is then stirred for 2 hours at room temperature The organic phase is again washed twice with potassium carbonate (2×10 ml) with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate filtered evaporated to dryness

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

Procedure: 258 mg (1 mmol) of (dibenzyl)acetyl chloride in 1 ml of toluene are added at room temperature to 140 mg (1.1 mmol) of N-hydroxypyridine-2-thione and 0.1 ml of pyridine in 5 ml of toluene. The mixture is maintained with stirring for 30 minutes. The filtered solution is added dropwise during 20 minutes to 1 ml of t-butylmercaptan in 20 ml of toluene at 80° C., and a vigorous stream of oxygen is passed into this solution. The reaction is continued for 1 hour at 80° C., and the reaction mixture is then stirred for 2 hours at room temperature before being poured into 10 ml of a saturated solution of potassium carbonate. The organic phase is again washed twice with potassium carbonate (2×10 ml), then with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate, filtered and evaporated to dryness. The crude product obtained is filtered on silica (100% CH2Cl2) to give 174 mg of the corresponding hydroxylated derivative. Yield 82%. The mixture is maintained The reaction is continued for 1 hour at 80° C. the reaction mixture is then stirred for 2 hours at room temperature The organic phase is again washed twice with potassium carbonate (2×10 ml) with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate filtered evaporated to dryness

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

Procedure: To a stirring suspension of 1.10 g of lithium aluminum hydride in 50 mL of diethyl ether under an argon atmosphere at 0° C. is slowly added a solution of 5.30 g of commercially available 1,3-diphenylacetone in 10.0 mL of diethyl ether with a 10 mL rinse. After 0.25 hours the grey suspension is warmed to room temperature. After 1.5 hours the reaction mixture is re-cooled to 0° C. and slowly treated with 1.2 mL of water followed by 5.0 mL of 1N sodium hydroxide. After 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings. The filtrate is concentrated under reduced pressure to afford 5.2 g, of the title product as a viscous, clear, colorless oil. This product may be used directly in the next reaction without further purification. Physical characteristics are as follows: rinse After 1.5 hours the reaction mixture is re-cooled to 0° C. slowly treated with 1.2 mL of water After 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings The filtrate is concentrated under reduced pressure to afford 5.2 g

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

Procedure: To a stirring suspension of 1.10 g of lithium aluminum hydride in 50 mL of diethyl ether under an argon atmosphere at 0° C. is slowly added a solution of 5.30 g of commercially available 1,3-diphenylacetone in 10.0 mL of diethyl ether with a 10 mL rinse. After 0.25 hours the grey suspension is warmed to room temperature. After 1.5 hours the reaction mixture is re-cooled to 0° C. and slowly treated with 1.2 mL of water followed by 5.0 mL of 1N sodium hydroxide. After 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings. The filtrate is concentrated under reduced pressure to afford 5.2 g, of the title product as a viscous, clear, colorless oil. This product may be used directly in the next reaction without further purification. Physical characteristics are as follows: rinse After 1.5 hours the reaction mixture is re-cooled to 0° C. slowly treated with 1.2 mL of water After 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings The filtrate is concentrated under reduced pressure to afford 5.2 g

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

Procedure: 258 mg (1 mmol) of (dibenzyl)acetyl chloride in 1 ml of toluene are added at room temperature to 140 mg (1.1 mmol) of N-hydroxypyridine-2-thione and 0.1 ml of pyridine in 5 ml of toluene. The mixture is maintained with stirring for 30 minutes. The filtered solution is added dropwise during 20 minutes to 1 ml of t-butylmercaptan in 20 ml of toluene at 80° C., and a vigorous stream of oxygen is passed into this solution. The reaction is continued for 1 hour at 80° C., and the reaction mixture is then stirred for 2 hours at room temperature before being poured into 10 ml of a saturated solution of potassium carbonate. The organic phase is again washed twice with potassium carbonate (2×10 ml), then with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate, filtered and evaporated to dryness. The crude product obtained is filtered on silica (100% CH2Cl2) to give 174 mg of the corresponding hydroxylated derivative. Yield 82%. The mixture is maintained The reaction is continued for 1 hour at 80° C. the reaction mixture is then stirred for 2 hours at room temperature The organic phase is again washed twice with potassium carbonate (2×10 ml) with 10 ml of water, twice with 10 ml of HCl (2N) and finally with twice 10 ml of water before being dried over sodium sulfate filtered evaporated to dryness