반응 #59963

반응 방정식

sodium hydrogen carbonate

DL-α-O-benzyl glycerol

3-pentanone

p-toluenesulfonic acid monohydrate

→

title compound

수율 67.1%

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

수율 67.1%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The generated precipitate was removed by filtration
2. 2
   농축the filtrate was concentrated
3. 3
   기타The 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
   농축A desired fraction was concentrated

실험 절차

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.

출처