(4-methyl-3-methylsulfonylphenyl)methanol

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

Procedure: A round bottom flask was charged with (4-methyl-3-(methylsulfonyl)phenyl)methanol (6.0 g, 30.14 mmol), toluene (70 mL). Diphenyl phosphoryl azide (7.8 mL, 36.1 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.3 mL, 36.1 mmol) were added at 0° C. and the reaction mixture was stirred over night at room temperature. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with EtOAc. The combined organic phases were concentrated under reduced pressure and the residue was purified by column chromatography to get the title compound (4 g, 62% yield). The solvent was removed under reduced pressure the residue was diluted with water extracted with EtOAc The combined organic phases were concentrated under reduced pressure the residue was purified by column chromatography

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

Procedure: A round bottom flask was charged with methyl-4-methyl-3-(methylsulfonyl)benzoate (1.5 g, 7.0 mmol) and methanol (15 mL) at 0° C. Sodium borohydride (3.7 g, 100 mmol) was added in portions and the reaction was stirred for 12 h at room temperature. The reaction was quenched with ice and extracted with MTBE. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash chromatography to get the title compound. The reaction was quenched with ice extracted with MTBE The combined organic phases were concentrated under reduced pressure the residue was purified by flash chromatography