ethylsulfonylbenzene

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: Potassium nitrate (4.46 g, 44.12 mmol) was added portion wise to a solution of ethylphenyl sulfone in concentrated HCl (25 mL) at room temperature; then the mixture was heated to reflux for one hour. After cooling, the mixture was poured onto ice and the precipitate was collected by filtration. The solid was washed with cold water (2×50 mL) and dried. 1H NMR (CDCl3) δ ppm 1.28 (3H), 3.45 (2H), 7.80 (1H), 8.21 (1H), 8.30 (1H), 8.85 (1H); MS (DCI) m/z 216 (M+H). then the mixture was heated to reflux for one hour After cooling the mixture was poured onto ice the precipitate was collected by filtration The solid was washed with cold water (2×50 mL) dried

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: Potassium nitrate (4.46 g, 44.12 mmol) was added portion wise to a solution of ethylphenyl sulfone in concentrated HCl (25 mL) at room temperature; then the mixture was heated to reflux for one hour. After cooling, the mixture was poured onto ice and the precipitate was collected by filtration. The solid was washed with cold water (2×50 mL) and dried. 1H NMR (CDCl3) δ ppm 1.28 (3H), 3.45 (2H), 7.80 (1H), 8.21 (1H), 8.30 (1H), 8.85 (1H); MS (DCI) m/z 216 (M+H). then the mixture was heated to reflux for one hour After cooling the mixture was poured onto ice the precipitate was collected by filtration The solid was washed with cold water (2×50 mL) dried

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

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

Procedure: A solution of n-butyllithium in hexanes (7.48 ml, 11.22 mmol) was added dropwise to a stirred solution of ethyl phenyl sulphone (1.87 g, 11 mmol) in THF (25 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.5 ml, 12.43 mmol) was added followed by methyl crotonate (2.0 ml, 18.7 mmol). The reaction mixture was stirred for 90 min., quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The organic extract was dried (Na2SO4) and concentrated to give 4-benzenesulfonyl-3-methylpentanoic acid methyl ester as a 8:1 mixture of diastereoisomers that was dissolved in dichloromethane (20 ml) and cooled using a ice-bath. A solution of diisobutyl aluminium hydride in dichloromethane (50.0 ml, 50.0 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. Ethyl acetate (10 ml) was added and the resulting mixture was poured into dichloromethane (200 ml) and cooled with an ice-bath. Water (4 ml) was added dropwise and the mixture was stirred for 30 min. dried over Na2SO4 for 30 min. filtered through a pad of Celite and concentrated. The residue was purified on silica gel (i-hexane-ethyl acetate) to give the title product. The reaction mixture was stirred for 90 min. quenched with sat. aqueous NH4Cl extracted into ethyl acetate The organic extract was dried (Na2SO4) concentrated

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

Procedure: A solution of n-butyllithium in hexanes (7.48 ml, 11.22 mmol) was added dropwise to a stirred solution of ethyl phenyl sulphone (1.87 g, 11 mmol) in THF (25 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.5 ml, 12.43 mmol) was added followed by methyl crotonate (2.0 ml, 18.7 mmol). The reaction mixture was stirred for 90 min., quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The organic extract was dried (Na2SO4) and concentrated to give 4-benzenesulfonyl-3-methylpentanoic acid methyl ester as a 8:1 mixture of diastereoisomers that was dissolved in dichloromethane (20 ml) and cooled using a ice-bath. A solution of diisobutyl aluminium hydride in dichloromethane (50.0 ml, 50.0 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. Ethyl acetate (10 ml) was added and the resulting mixture was poured into dichloromethane (200 ml) and cooled with an ice-bath. Water (4 ml) was added dropwise and the mixture was stirred for 30 min. dried over Na2SO4 for 30 min. filtered through a pad of Celite and concentrated. The residue was purified on silica gel (i-hexane-ethyl acetate) to give the title product. The reaction mixture was stirred for 90 min. quenched with sat. aqueous NH4Cl extracted into ethyl acetate The organic extract was dried (Na2SO4) concentrated

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

Procedure: Potassium nitrate (4.46 g, 44.12 mmol) was added portion wise to a solution of ethylphenyl sulfone in concentrated HCl (25 mL) at room temperature; then the mixture was heated to reflux for one hour. After cooling, the mixture was poured onto ice and the precipitate was collected by filtration. The solid was washed with cold water (2×50 mL) and dried. 1H NMR (CDCl3) δ ppm 1.28 (3H), 3.45 (2H), 7.80 (1H), 8.21 (1H), 8.30 (1H), 8.85 (1H); MS (DCI) m/z 216 (M+H). then the mixture was heated to reflux for one hour After cooling the mixture was poured onto ice the precipitate was collected by filtration The solid was washed with cold water (2×50 mL) dried