Reacción #520065

Ecuación de reacción

water

5-hexynoic acid

3-methyl-3-oxetane methanol

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

Rendimiento 95.4%

5-Hexynoic Acid (3-Methyloxetan-3-yl)methyl Ester

Rendimiento 95.4%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder cooling with ice
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe organic layer was washed by water
4. 4
   Secadoan aqueous saturated solution of sodium chloride, sucessively, dried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified with silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Procedimiento

To a solution of 5-hexynoic acid (10.0 g) and 3-methyl-3-oxetane methanol (10.0 g) in methylene chloride (50 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (20.5 g), and 4-dimethylaminopyridine (1.09 g) were added under cooling with ice. The mixture was stirred at room temperature for 45 minutes. The reaction mixture was poured into iced water and extracted with ethyl acetate. The organic layer was washed by water and an aqueous saturated solution of sodium chloride, sucessively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified with silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the title compound (16.7 g) having the following physical data.

Fuente