Formaldehyde → 4-[Ethyl-[(4-methoxyphenyl)methyl]amino]but-2-yn-1-ol

Participants

Reaction Steps

A mixture of N-ethyl-4-methoxybenzenemethanamine (13.3 g, 80.6 mmol), paraformaldehyde (3.63 g), propargyl alcohol (6.33 g, 113 mmol) and CuCl (0.311 g) in 350 mL of 1,4-dioxane was stirred at reflux for 30 min. The reaction mixture was cooled to room temperature and concentrated. The residue was diluted with 200 mL of 50% NH4OH and extracted with EtOAc. The combined extracts were washed with water, brine, dried and concentrated. The residue was chromatographed on silica gel (elution with 2.5% MeOH in CH2Cl2 and then 5% MeOH in CH2Cl2) to afford the product V (15.1 g, 81% yield) as an oil.

Provenance & Evidence