Methane → HCID 15078769, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 1,2-dihydroxy-1-cyclobutene-3,4-dione (15.0 g, 131.5 mmol), 45 mL of 1-butanol and 30 mL of toluene was heated at reflux under a nitrogen atmosphere with stirring under a Dean-Stark Water separator until water stopped passing over. The reaction mixture was then cooled to 0° C. and a solution of 3-amino-1-propanol (9.88 g, 131.5 mmol) in 10 mL of 1-butanol was added dropwise. After 1 hour at ambient temperature, charcoal was added and the mixture filtered through a pad of diatomaceous earth. The filtrate was evaporated under reduced pressure to give 28.9 g of the title compound as an oil. A portion of the product (24.7 g) was dissolved in dichloromethane and filtered through a pad of about 200 g of silica gel. The pad was washed with 1.6 L of dichloromethane:methanol (9:1), and the filtrate was evaporated in vacuo to produce 22.7 g of the title compound.

Provenance & Evidence