Formaldehyde → HCID 59438395, compound

Participants

Reaction Steps

To a stirred room temperature solution of 164 ul (1.940 mmol) methylamine (41% in water) in 1 ml dioxane was added 141 ul (1.940 mmol) formaldehyde (37% in water) dropwise (exothermic reaction). The mixture was stirred for 5 min and then a solution of 0.5 g (1.940 mmol) rac-4-(3-chloro-phenyl)-4-nitro-butyric acid methyl ester in 1.5 ml dioxane was added at once. The mixture was stirred at 65° C. for 6 h. The mixture was cooled to room temperature, ethyl acetate and a saturated NaCl solution were added. Aqueous phase was extracted 2 times with ethyl acetate. Combined organic phases were washed with a saturated NaCl solution, dried over sodium sulfate and concentrated in vacuo. The crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 395 mg (76%) of the title compound as a colorless oil. MS (m/e): 269.2 (MH+).

Provenance & Evidence