Reacción #2074285

Ecuación de reacción

(2R)-3-(benzyloxy)propane-1,2-diol

1,2-dichloroethane

sodium hydroxide

1,2-dichloroethane

sodium hydroxide

1,2-dichloroethane

→

title compound

(2S)-2-[(benzyloxy)methyl]-1,4-dioxane

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 8 h
2. 2
   workup.WAITAfter 72 h
3. 3
   Lavadowashed with water and brine
4. 4
   Secadodried over sodium sulfate
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by flash column chromatography (silica, ethylacetate/hexanes)

Procedimiento

(2R)-3-(benzyloxy)propane-1,2-diol (2.00 g, 11.0 mmol) and tetrabutylammonium bromide (708 mg, 2.20 mmol) were dissolved in 50 mL of 1,2-dichloroethane, then 50 mL of a 50% (w/w) aqueous sodium hydroxide solution was added quickly and the mixture was heated to 50° C. After 18 h, an additional 50 mL of 1,2-dichloroethane and 50 mL of 50% (w/w) sodium hydroxide solution was added. After 8 h, additional 50 mL of 1,2-dichloroethane was added. After 72 h, the mixture was diluted in diethyl ether, washed with water and brine, then dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (silica, ethylacetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 7.26-7.35 (m, 5H); 4.51-4.56 (m, 2H); 3.72-3.82 (m, 4H); 3.67-3.71 (m, 1H); 3.58-3.64 (m, 1H); 3.38-3.48 (m, 3H).

Fuente