(3-methylsulfonylphenyl)methanol

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:

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:

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

Procedure: NaBH4 is added to a solution of 750 mg (4.08 mmol) 3-methanesulphonyl-benzaldehyde in 20 ml ethanol (see P. L. Ornstein, T. J. Bleisch, M. B. Arnold, R. A. Wright, B. G. Johnson, J. P. Tizzano, D. R. Helton, M. J. Kallman, D. D. Schoepp, M. Herin, J. Med. Chem. 1998, 41(3), 358-378 or B. Eistert, W. Schade, H. Selzer, Ber. 1964, 97(5), 1470-81). The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is poured into water and extracted three times with ethyl acetate. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, used in the next step without further purification. extracted three times with ethyl acetate The combined organic layers are washed with water and brine dried filtered concentrated in vacuo

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.267 ml (3.45 mmol) methanesulphonyl-chloride is added to o a solution of 584 mg (3.14 mmol) (3-methanesulphonyl-phenyl)-methanol and 0.66 ml (4.71 mmol) triethylamine in 6 ml dichloromethane. This reaction mixture is stirred at room temperature for 1 h and at 50° C. for additional 3 h. The reaction mixture is then poured into water and extracted twice with dichloromethane. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, which is used in the next step without further purification. extracted twice with dichloromethane The combined organic layers are washed with water and brine dried filtered concentrated in vacuo

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

Procedure: A solution of 3-(methylsulfonyl)benzoic acid (1.0 g, 5.0 mmol) in anhydrous THF (25 mL) was treated with BH3.THF (1 M solution, 7.5 mL) at room temperature. The reaction was stirred for 12 hours before it was quenched by slow addition of MeOH. The solvent was removed and the residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2) to give the product (0.84 g, 90% yield). 1H NMR (300 MHz, CDCl3) δ: 3.06 (s, 3 H), 4.81 (d, J=6.0 Hz, 2 H), 7.54–7.59 (m, 1 H), 7.65–7.68 (m, 1 H), 7.85–7.88 (m, 1 H), 7.96 (s, 1 H). was quenched by slow addition of MeOH The solvent was removed the residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2)

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

Procedure: A solution of [3-(methylsulfonyl)phenyl]methanol (680 mg, 3.66 mmol) in anhydrous CH2Cl2 (20 mL) was treated with PCC (1.03 g, 4.75 mmol) at room temperature for 2 hours. The solvent was removed and the residue was purified by flash column chromatography (20–60% EtOAc in hexanes) to give the product (500 mg, 74% yield). 1H NMR (300 MHz, CDCl3) δ: 3.13 (s, 3 H), 7.77–7.82 (m, 1 H), 8.18–8.24 (m, 2 H), 8.46–8.48 (m, 1 H), 10.12 (s, 1 H). The solvent was removed the residue was purified by flash column chromatography (20–60% EtOAc in hexanes)