Reacción #59963

Ecuación de reacción

sodium hydrogen carbonate

DL-α-O-benzyl glycerol

3-pentanone

p-toluenesulfonic acid monohydrate

→

title compound

Rendimiento 67.1%

4-((benzyloxy)methyl)-2,2-diethyl-1,3-dioxolane

Rendimiento 67.1%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe generated precipitate was removed by filtration
2. 2
   Concentraciónthe filtrate was concentrated
3. 3
   OtroThe obtained residue was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 3/1 gradient)
4. 4
   ConcentraciónA desired fraction was concentrated

Procedimiento

To a tetrahydrofuran (30 ml) solution of DL-α-O-benzyl glycerol (3 g, 16.5 mmol), 3-pentanone (17.5 ml, 165 mmol) and p-toluenesulfonic acid monohydrate (300 mg, 1.58 mmol) were added at room temperature and the mixture was stirred at the same temperature for 22 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (5 ml) was added to adjust pH to about 8. The generated precipitate was removed by filtration and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 3/1 gradient). A desired fraction was concentrated to obtain the title compound (2.77 g, 67.1% yield) as a colorless oil.

Fuente