Reaktion #518119

Reaktionsgleichung

Methyl 2,4-dibromo-2,4-dideoxy-L-threonate

potassium acetate

→

title compound

Ausbeute 99.3%

Methyl (2S,3S)-4-acetoxy-2,3-epoxybutanoate

Ausbeute 99.3%

Lösungsmittel

ethyl acetate

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   WaschenThe filter cake is washed with ethyl acetate (250 mL)
3. 3
   WaschenThe combined ethyl acetate portion is washed with saturated sodium bicarbonate solution (500 mL) and saturated brine (2×500 mL)
4. 4
   Trocknendried over magnesium sulfate
5. 5
   SonstigeThe solvent is removed

Vorschrift

The general procedure of Manchand, et. al. (Manchand, et al., 1988) is employed. Methyl 2,4-dibromo-2,4-dideoxy-L-threonate (131 g, 474 mmol) is added to a stirred solution of potassium acetate (102 g, 1.04 mol) and potassium iodide (3.94 g, 23.8 mmol) in dimethyl formamide (500 mL). This mixture is stirred under nitrogen gas at 50-55° C. for 4 hours and overnight at room temperature. The reaction mixture is diluted with ethyl acetate (1 L) and filtered. The filter cake is washed with ethyl acetate (250 mL). The combined ethyl acetate portion is washed with saturated sodium bicarbonate solution (500 mL) and saturated brine (2×500 mL) and dried over magnesium sulfate. The solvent is removed to yield the title compound as a dark oil (82.0 g, 99% theoretical yield).

Quelle