반응 #309458

반응 방정식

(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

용매

diethyl ether

반응 조건

후처리

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

실험 절차

(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).

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