2-(4-methylsulfonylphenyl)ethanol

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

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: Methyl 2-(4-hydroxybenzyl)butanoate (0.50 g; 2.5 mmole) and 2-[4-(methylsulfonyl)phenyl]ethanol (0.52 g, 2.5 mmole) were mixed in dichloromethane (10 ml). ADDP (0.76 g, 3.0 mmole) was added followed by addition of triphenylphosphine ((0.79 g, 3.0 mmole). The reaction was interrupted after 16 hours. Triphenylphosphine oxide formed in the reaction was filtered off and the filtrate was evaporated. Chromatography of the crude material from methanol and dichloromethane, gradient eluation from 0-32% gave 0.64 g (66% yield) of the product.

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

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

Procedure: 1.83 g (15 mmole) 4-hydroxybenzaldehyde was dissolved in 35 ml dichloromethane under argon atmosphere. 1.5 g (7.5 mmole) 2-[4-(methylsulfonyl)phenyl]-1-ethanol was added followed by 3.93 g (15 mmole) triphenylphosphine and 3.78 g (15 mmole) 1,1-(azodicarbonyl)dipiperidine. The reaction mixture was stirred at room temperature and after 2 hours a precipitate is observed. The reaction was disrupted after 5 hours and the reaction mixture was filtered. The filtrate was purified by chromatography on silica gel using dichloromethane:methanol (98:2) as eluent giving 1.66 g (yield 54.5%) of 4-[2-(4-formylphenoxy)ethyl]phenyl methyl sulfone. The reaction was disrupted after 5 hours the reaction mixture was filtered The filtrate was purified by chromatography on silica gel

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (47 mmole) 4-(methylsulfonyl)phenyl acetic acid was dissolved in 40 ml tetrahydrofuran and the solution was cooled to −10° C. At this temperature 4-(methylsulfonyl)phenyl acetic acid precipitates. 47 ml 1 M borane-tetrahydrofuran complex was added slowly. The reaction mixture was allowed to reach room temperature and the reaction was followed by TLC. After completion 100 ml methanol was added and the solvents were evaporated. The residue was dissolved in dichloromethane and washed with sodium hydroxide. The organic phase was dried, filtered and evaporated in vacuo to give 7.5 g (yield 79.7%) of 2-[4-(methylsulfonyl)phenyl]-1-ethanol. At this temperature 4-(methylsulfonyl)phenyl acetic acid precipitates 47 ml 1 M borane-tetrahydrofuran complex was added slowly to reach room temperature After completion 100 ml methanol was added the solvents were evaporated The residue was dissolved in dichloromethane washed with sodium hydroxide The organic phase was dried filtered evaporated in vacuo

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

Procedure: Methyl 2-(4-hydroxybenzyl)butanoate (0.50 g; 2.5 mmole) and 2-[4-(methylsulfonyl)phenyl]ethanol (0.52 g, 2.5 mmole) were mixed in dichloromethane (10 ml). ADDP (0.76 g, 3.0 mmole) was added followed by addition of triphenylphosphine ((0.79 g, 3.0 mmole). The reaction was interrupted after 16 hours. Triphenylphosphine oxide formed in the reaction was filtered off and the filtrate was evaporated. Chromatography of the crude material from methanol and dichloromethane, gradient eluation from 0-32% gave 0.64 g (66% yield) of the product.