(1-methylsulfonylcyclopropyl)methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-bromo-3,5-dimethylphenol, (306 mg, 1.52 mmol), (1-Methanesulfonyl-cyclopropyl)-methanol (228 mg, 1.52 mmol), and triphenylphosphine (399 mg, 1.52 mmol) are suspended in dry tetrahydrofuran (10 mL) and cooled to 0° C. Di-tert-butylazodicarboxylate (350 mg, 1.52 mmol) is added and the mixture stirred at 50° C. for 48 hours then at room temperature for a further 48 hours. The mixture is concentrated under vacuum then partitioned between water and dichloromethane, The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-20% ethyl acetate in cyclohexane) to give the title compound as a crude material which was used without further purification (Yield 664 mg). at room temperature for a further 48 hours The mixture is concentrated under vacuum then partitioned between water and dichloromethane The organic phase is dried the solvent removed under vacuum The residue is purified by flash chromatography (0-20% ethyl acetate in cyclohexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methanesulfonyl-cyclopropanecarboxylic acid ethyl ester (1 g, 5.2 mmol) is dissolved in dry tetrahydrofuran (20 mL) and cooled to 0° C. Lithium aluminium hydride (237 mg, 6.24 mmol) is added, the mixture allowed to warm to room temperature and stirred overnight. The mixture is cooled to 0° C. and saturated aqueous sodium sulfate solution is added with stirring. The precipitated solids are removed by filtration and the filtrate is partitioned between ethyl acetate and water. The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (ethyl acetate) to give the title compound (Yield 317 mg). to warm to room temperature The mixture is cooled to 0° C. with stirring The precipitated solids are removed by filtration the filtrate is partitioned between ethyl acetate and water The organic phase is dried the solvent removed under vacuum The residue is purified by flash chromatography (ethyl acetate)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methanesulfonyl-cyclopropanecarboxylic acid ethyl ester (1 g, 5.2 mmol) is dissolved in dry tetrahydrofuran (20 mL) and cooled to 0° C. Lithium aluminium hydride (237 mg, 6.24 mmol) is added, the mixture allowed to warm to room temperature and stirred overnight. The mixture is cooled to 0° C. and saturated aqueous sodium sulfate solution is added with stirring. The precipitated solids are removed by filtration and the filtrate is partitioned between ethyl acetate and water. The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (ethyl acetate) to give the title compound (Yield 317 mg). to warm to room temperature The mixture is cooled to 0° C. with stirring The precipitated solids are removed by filtration the filtrate is partitioned between ethyl acetate and water The organic phase is dried the solvent removed under vacuum The residue is purified by flash chromatography (ethyl acetate)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-bromo-3,5-dimethylphenol, (306 mg, 1.52 mmol), (1-Methanesulfonyl-cyclopropyl)-methanol (228 mg, 1.52 mmol), and triphenylphosphine (399 mg, 1.52 mmol) are suspended in dry tetrahydrofuran (10 mL) and cooled to 0° C. Di-tert-butylazodicarboxylate (350 mg, 1.52 mmol) is added and the mixture stirred at 50° C. for 48 hours then at room temperature for a further 48 hours. The mixture is concentrated under vacuum then partitioned between water and dichloromethane, The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-20% ethyl acetate in cyclohexane) to give the title compound as a crude material which was used without further purification (Yield 664 mg). at room temperature for a further 48 hours The mixture is concentrated under vacuum then partitioned between water and dichloromethane The organic phase is dried the solvent removed under vacuum The residue is purified by flash chromatography (0-20% ethyl acetate in cyclohexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methanesulfonyl-cyclopropanecarboxylic acid ethyl ester (1 g, 5.2 mmol) is dissolved in dry tetrahydrofuran (20 mL) and cooled to 0° C. Lithium aluminium hydride (237 mg, 6.24 mmol) is added, the mixture allowed to warm to room temperature and stirred overnight. The mixture is cooled to 0° C. and saturated aqueous sodium sulfate solution is added with stirring. The precipitated solids are removed by filtration and the filtrate is partitioned between ethyl acetate and water. The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (ethyl acetate) to give the title compound (Yield 317 mg). to warm to room temperature The mixture is cooled to 0° C. with stirring The precipitated solids are removed by filtration the filtrate is partitioned between ethyl acetate and water The organic phase is dried the solvent removed under vacuum The residue is purified by flash chromatography (ethyl acetate)