2-(2-methoxyphenyl)oxirane

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: A mixture of 9.7 g of sodium hydride, 38 g of trimethylsulfonium iodide and 25.2 g (0.185 mol) of o-methoxybenzaldehyde is reacted to give o-methoxystyrene oxide. is reacted

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

Procedure: A mixture of 9.7 g of sodium hydride, 38 g of trimethylsulfonium iodide and 25.2 g (0.185 mol) of o-methoxybenzaldehyde is reacted to give o-methoxystyrene oxide. is reacted

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1000-mL 3-necked round-bottom flask was placed DMSO (400 mL) and sodium hydride (7 g, 175.00 mmol, 1.19 equiv, 60%). This was followed by the addition of S,S-dimethylmethanesulfinyl iodide (38 g, 172.67 mmol, 1.18 equiv). The mixture was stirred for 1 h at 40° C. To this was added a solution of 2-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 equiv) in DMSO (100 mL) dropwise with stirring at 15° C. The resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 400 mL of NH4Cl (aq.). The resulting solution was extracted with 1000 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1000 mL of H2O. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. Purification afforded 14 g (63%) of 2-(2-methoxyphenyl)oxirane as a yellow oil. Into a 1000-mL 3-necked round-bottom flask was placed with stirring at 15° C The resulting solution was stirred for 1 h at room temperature The reaction was then quenched by the addition of 400 mL of NH4Cl (aq.) The resulting solution was extracted with 1000 mL of ethyl acetate The resulting mixture was washed with 1000 mL of H2O The mixture was dried over anhydrous sodium sulfate concentrated under vacuum Purification

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1000-mL 3-necked round-bottom flask was placed DMSO (400 mL) and sodium hydride (7 g, 175.00 mmol, 1.19 equiv, 60%). This was followed by the addition of S,S-dimethylmethanesulfinyl iodide (38 g, 172.67 mmol, 1.18 equiv). The mixture was stirred for 1 h at 40° C. To this was added a solution of 2-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 equiv) in DMSO (100 mL) dropwise with stirring at 15° C. The resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 400 mL of NH4Cl (aq.). The resulting solution was extracted with 1000 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1000 mL of H2O. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. Purification afforded 14 g (63%) of 2-(2-methoxyphenyl)oxirane as a yellow oil. Into a 1000-mL 3-necked round-bottom flask was placed with stirring at 15° C The resulting solution was stirred for 1 h at room temperature The reaction was then quenched by the addition of 400 mL of NH4Cl (aq.) The resulting solution was extracted with 1000 mL of ethyl acetate The resulting mixture was washed with 1000 mL of H2O The mixture was dried over anhydrous sodium sulfate concentrated under vacuum Purification

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

Procedure: A mixture of 33,5 g. (0.185 mol) of 3,4-dimethoxyphenylethylamine and 28 g. of o-methoxystyrene oxide is heated with stirring under argon on a steam bath overnight. A sample is chromatographed to obtain a pure sample of the product. This pure seed and 200 ml. of 2:1 ethyl acetatepetroleum ether are added to the reaction mixture. Chilling and stirring yields the product N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methoxyphenyl)ethylamine. m.p. 88° C. A mixture of 33,5 g A sample is chromatographed to obtain a pure sample of the product of 2:1 ethyl acetatepetroleum ether are added to the reaction mixture Chilling stirring

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

Procedure: A mixture of 33,5 g. (0.185 mol) of 3,4-dimethoxyphenylethylamine and 28 g. of o-methoxystyrene oxide is heated with stirring under argon on a steam bath overnight. A sample is chromatographed to obtain a pure sample of the product. This pure seed and 200 ml. of 2:1 ethyl acetatepetroleum ether are added to the reaction mixture. Chilling and stirring yields the product N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methoxyphenyl)ethylamine. m.p. 88° C. A mixture of 33,5 g A sample is chromatographed to obtain a pure sample of the product of 2:1 ethyl acetatepetroleum ether are added to the reaction mixture Chilling stirring

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

Procedure: Following the procedure of Example 7, 9.7 g. of sodium hydride, 38 g. of trimethylsulfonium iodide and 25.2 g. (0.185 mol) of o-methoxybenzaldehyde are reacted to give o-methoxystyrene oxide.

Conditions: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 2-(2-methoxyphenyl)oxirane (5.60 g, 37.3 mmol) in toluene (65 ml) was added 4-hydroxybenzaldehyde (6.80 g, 56.0 mmol), 1M NaOH (65 ml) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. overnight. The reaction was allowed to cool to RT and it was then extracted with EtOAc (2×150 ml). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light oil was adsorbed onto silica gel and chromatographed eluting with 30-40% EtOAc/hexanes. There are 2 major spots. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.71 g (17%) the regioisomer as a brown oil. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 2.05 g (20%) of the title compound as a yellow solid. to cool to RT it was then extracted with EtOAc (2×150 ml) The combined extracts were washed with brine dried (Na2SO4) filtered evaporated in vacuo chromatographed eluting with 30-40% EtOAc/hexanes Fractions containing the higher Rf spot evaporated in vacuo to give 1.71 g (17%) the regioisomer as a brown oil Fractions containing the lower Rf spot evaporated in vacuo

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

Procedure: To a solution of 2-vinyl anisole (5.0 g, 0.037 mol) and acetic acid (2.1 mL, 37 mmol) in dioxane (33 ml) and H2O (78 ml) at 0° C. was added N-bromosuccinimide (7.30 g, 40.1 mmol) in three portions. The reaction was allowed to warm to R.T. and after 1 hour, 2M NaOH (50 ml) was added. The reaction was left to stir at RT overnight. The reaction mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 7.56 g slightly tinted oil. This was dissolved in dioxane, 2N NaOH was added and the reaction was stirred at RT overnight. Repeated aqueous work-up gave 5.60 g of the title compound as a nearly colorless oil. The reaction was left The reaction mixture was partitioned between water and EtOAc the aqueous phase was extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) filtered evaporated in vacuo to give 7.56 g slightly tinted oil the reaction was stirred at RT overnight

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

Procedure: To a solution of 2-vinyl anisole (5.0 g, 0.037 mol) and acetic acid (2.1 mL, 37 mmol) in dioxane (33 ml) and H2O (78 ml) at 0° C. was added N-bromosuccinimide (7.30 g, 40.1 mmol) in three portions. The reaction was allowed to warm to R.T. and after 1 hour, 2M NaOH (50 ml) was added. The reaction was left to stir at RT overnight. The reaction mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 7.56 g slightly tinted oil. This was dissolved in dioxane, 2N NaOH was added and the reaction was stirred at RT overnight. Repeated aqueous work-up gave 5.60 g of the title compound as a nearly colorless oil. The reaction was left The reaction mixture was partitioned between water and EtOAc the aqueous phase was extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) filtered evaporated in vacuo to give 7.56 g slightly tinted oil the reaction was stirred at RT overnight