methyl 2-azidoacetate

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:

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: 4-Benzyloxybenzaldehyde (10.0 g) and methyl azidoacetate (21.7 g) are dissolved in 157 ml of methanol and cooled to -10° (ice-acetone bath). Then sodium methoxide (43.1 ml, 25% in methanol) is added dropwise such that the reaction temperature does not rise above -5°. After 2 hr, the cooling bath is removed and the reaction is warmed to 20°-25°. When no starting material remains by TLC, the reaction is diluted with ether and washed with saturated aqueous ammonium chloride. The organic layer is washed with water, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (hexane to 5% ethyl acetate/hexane) gives the title compound. does not rise above -5° the cooling bath is removed the reaction is warmed to 20°-25° the reaction is diluted with ether washed with saturated aqueous ammonium chloride The organic layer is washed with water, saline dried over anhydrous sodium sulfate concentrated under reduced pressure Purification by flash column chromatography (hexane to 5% ethyl acetate/hexane)

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

Procedure: While 23 ml of sodium methoxide (28% solution in methanol) in 40 ml of anhydrous methanol was stirred vigorously, 40 ml of a mixed methanol solution containing 4.0 g (21.1 mmol) of 2,5-dimethoxybenzaldehyde and 9.7 g (84.2 mmol) of methyl azidoacetate was added dropwise at -15° C. After completion of the addition, the reaction mixture was stirred for 2 hours. Then the reaction mixture was poured into a saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to provide 3.1 g of methyl 2,5-dimethoxyphenyl-α-azidocinnamate. was added dropwise at -15° C After completion of the addition extracted with ethyl acetate The extract was washed with water dried over magnesium sulfate After distilling off the solvent the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)

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

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