[4-(methylsulfonylmethyl)phenyl]methanol

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

Procedure: Triphenylphosphine (5.71 g, 21.8 mmol), carbon tetrachloride (8.4 mL, 87 mmol), and tetrahydrofuran (12 mL) were combined in a round bottom flask under argon and stirred at room temperature for 10 minutes. A heterogeneous mixture of (4-methanesulfonylmethyl-phenyl)-methanol (2.18 g, 10.9 mmol) and tetrahydrofuran (37 mL) were added to the reaction mixture, and then the mixture was heated at 75° C. for 3 hours. The reaction mixture was cooled to room temperature, and then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give the crude product as an oily solid. A solution of this crude product and dichloromethane was concentrated over silica gel, and the resulting silica gel supported crude product was loaded onto a RediSep® Flash column. Flash chromatography (25%-40% ethyl acetate in hexanes) afforded 1.59 g (67%) of 1-chloromethyl-4-methanesulfonylmethyl benzene as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.47 (d, J=8.2 Hz, 2 H), 7.41 (d, J=8.2 Hz, 2 H), 4.78 (s, 2 H), 4.50 (s, 2 H), 2.91 (s, 3 H). were added to the reaction mixture the mixture was heated at 75° C. for 3 hours The reaction mixture was cooled to room temperature partitioned between ethyl acetate and water The organic phase was dried over MgSO4 filtered concentrated to give the crude product as an oily solid A solution of this crude product and dichloromethane was concentrated over silica gel

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

Procedure: A 1.0 M solution of diisobutylaluminum hydride in toluene (44 mL, 44 mmol) was added slowly drop-wise to a 0° C. solution of methyl 4-(methanesulfonylmethyl)benzoate (4.00 g, 17.5 mmol) and toluene (220 mL). After the addition was complete, the reaction mixture was warmed to room temperature, then stirred at room temperature for 16 hours. After this time, thin-layer chromatography indicated some starting material to remain. The reaction mixture was cooled to 0° C., then additional 1.0 M diisobutylaluminum hydride in toluene (44 mL, 44 mmol) was added slowly drop-wise to the cold reaction mixture. The reaction mixture was warmed to room temperature, and then stirred for 20 minutes. The reaction mixture was again cooled to 0° C. Ethyl acetate (50 mL) was added followed by methanol (1 mL). The reaction mixture was allowed to stand for 6 minutes at 0° C., during which time the mixture became cloudy and thick. A saturated aqueous solution of sodium potassium tartrate was added, and the heterogeneous mixture was warmed to room temperature. Water and additional ethyl acetate (50 mL) were added. The organic phase was separated, dried over MgSO4, filtered, and concentrated to give 2.18 g (62%) of (4-methane-sulfonylmethyl-phenyl)-methanol as a white solid. After the addition The reaction mixture was cooled to 0° C. The reaction mixture was warmed to room temperature stirred for 20 minutes The reaction mixture was again cooled to 0° C to stand for 6 minutes at 0° C., during which time the heterogeneous mixture was warmed to room temperature The organic phase was separated dried over MgSO4 filtered concentrated