methyl 4-(phenylsulfanylmethyl)benzoate

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

Procedure: Methyl 4-(phenylsulfanylmethyl)benzoate (1.07 g) was dissolved in THF (14 mL), added with lithium aluminum hydride (200 mg) in small portions under ice cooling, and stirred for 40 minutes at the same temperature. Under ice cooling, sodium sulfate decahydrate was added in small portions and filtered through Celite. The solvent was evaporated under reduced pressure. The residues were suspended in hexane and collected by filtration to obtain the title compound (910 mg) as a white powder. filtered through Celite The solvent was evaporated under reduced pressure collected by filtration

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

Procedure: To a mixture of benzenethiol (1.3 mL, 13.1 mmol) and potassium tert-butoxide (1.47 g, 13.1 mmol) in DMF (50 mL) at 0° C. was added 4-(bromomethyl)benzoic acid methyl ester (3.0 g, 13.1 mmol), and the mixture was stirred at room temperature for 1 hour. After stirring at 80-90° C. overnight, the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water (30 mL) and extracted with CH2Cl2 (200 mL). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by MPLC on silica gel (10% EtOAc in hexanes) to afford the titled compound (2.74 g, 81%) as a white solid. After stirring at 80-90° C. overnight the reaction mixture was evaporated to dryness under reduced pressure The residue was dissolved in water (30 mL) extracted with CH2Cl2 (200 mL) The organic layer was dried (MgSO4) evaporated under reduced pressure The crude product was purified by MPLC on silica gel (10% EtOAc in hexanes)

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

Procedure: Methyl 4-(phenylsulfanylmethyl)benzoate (1.07 g) was dissolved in THF (14 mL), added with lithium aluminum hydride (200 mg) in small portions under ice cooling, and stirred for 40 minutes at the same temperature. Under ice cooling, sodium sulfate decahydrate was added in small portions and filtered through Celite. The solvent was evaporated under reduced pressure. The residues were suspended in hexane and collected by filtration to obtain the title compound (910 mg) as a white powder. filtered through Celite The solvent was evaporated under reduced pressure collected by filtration