2-(methoxymethyl)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:

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 solution of 4-bromopyrazole (200 mg, 1.36 mmol) in methyl glycidyl ether (510 mg, 5.79 mmol) was heated at 100° C. for 70 minutes. After cooling to r.t., the excess methyl glycidyl ether was removed in vacuo to give the title compound (165 mg, 52%) as a clear yellow liquid. δH (CDCl3) 3.21-3.24 (1H, m), 3.31-3.35 (2H, m), 3.38 (3H, s), 4.08-4.30 (3H, m), 7.47-7.50 (2H, m). LCMS (ES+) 235, 237 (M+H)+. the excess methyl glycidyl ether was removed in vacuo

Conditions: temp:98.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-pyrazoleboronic acid pinacol ester (4.24 g, 21.9 mmol) and glycidyl methyl ether (7.94 g, 76.6 mmol) was heated to 98° C. for 4 h. It was cooled to r.t. and concentrated in vacuo to give the title compound (6.7 g, quantitative) as a yellow oil. δH (CDCl3) 1.32 (12H, s), 3.37 (3H, s), 3.12-3.54 (3H, m), 4.08-4.37 (3H, m), 7.73 (1H, s), 7.80 (1H, s). It was cooled to r.t. concentrated in vacuo

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Benzylethanolamine (459 g) is mixed with 1,2-epoxy-3-methoxypropane (422 g) and the mixture is stirred at 50° C. for 16 hours and thereafter the excess 1,2-epoxy-3-methoxypropane is distilled off under reduced pressure. The residue is dissolved in 1,4-dioxane (3 liters) and thereto are added powdery potassium hydroxide (692.5 g) and tris(3,6-dioxaheptyl)amine (11.4 g). To the mixture is added dropwise with stirring a solution of p-toluenesulfonyl chloride (809.4 g) in 1,4-dioxane (2 liters) over a period of 1.5 hour, during which the temperature of the reaction mixture raises and the solvent is refluxed. After the dropwise addition, the mixture is stirred for 2 hours, and the undissolved materials are filtered off and washed with ethyl acetate. The filtrate and the washing liquid are combined and distilled under reduced pressure to remove the solvent. To the residue are added water (600 ml) and conc. hydrochloric acid (300 ml) to make acidic. The aqueous layer is washed with ethyl acetate, made strongly basic by adding sodium hydroxide (160 g) under ice cooling and extracted with ethyl acetate. The ethyl acetate layer is washed with saturated saline solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The obtained residue is distilled under reduced pressure to give the title compound (391.3 g) as colorless liquid. the excess 1,2-epoxy-3-methoxypropane is distilled off under reduced pressure The residue is dissolved in 1,4-dioxane (3 liters) are added powdery potassium hydroxide (692.5 g) and tris(3,6-dioxaheptyl)amine (11.4 g) To the mixture is added dropwise with stirring a solution of p-toluenesulfonyl chloride (809.4 g) in 1,4-dioxane (2 liters) over a period of 1.5 hour during which the temperature of the reaction mixture raises the solvent is refluxed After the dropwise addition the mixture is stirred for 2 hours the undissolved materials are filtered off washed with ethyl acetate distilled under reduced pressure to remove the solvent To the residue are added water (600 ml) and conc. hydrochloric acid (300 ml) The aqueous layer is washed with ethyl acetate by adding sodium hydroxide (160 g) under ice cooling extracted with ethyl acetate The ethyl acetate layer is washed with saturated saline solution dried over anhydrous magnesium sulfate distilled under reduced pressure to remove the solvent The obtained residue is distilled under reduced pressure

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

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

Procedure: Starting materials: benzyl amine and 2-(methoxymethyl)oxirane

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

Procedure: Starting materials: benzyl amine and 2-(methoxymethyl)oxirane

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

Procedure: Starting materials: benzyl amine and 2-(methoxymethyl)oxirane