Reaktion #56744

Reaktionsgleichung

(R)-glycidyl tosylate

2′,3′,4′-trihydroxyacetophenone

potassium carbonate

→

title compound

1-[5-Hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter removal of the solvent in vacuum
2. 2
   Extraktionwas then extracted with ethyl acetate (4×300 mL)
3. 3
   TrocknenThe combined organic layers were dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporate to dryness in vacuum
6. 6
   SonstigeThe crude brown oil thus obtained
7. 7
   Sonstigechromatographed on silica gel with 40% hexane/ethyl acetate as eluent

Vorschrift

To a solution of 2′,3′,4′-trihydroxyacetophenone (10.6 g, 63.0 mmole) in DMF (75 mL) was added potassium carbonate (17.4 g, 126 mmole). After 5 minutes (R)-glycidyl tosylate (9.67 g, 42.3 mmole) was added, then the heterogeneous mixture was heated to 70° C. for 3 hours. After removal of the solvent in vacuum, the residue was taken into water (800 mL) and was then extracted with ethyl acetate (4×300 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporate to dryness in vacuum. The crude brown oil thus obtained was column chromatographed on silica gel with 40% hexane/ethyl acetate as eluent to give the (S)-enantiomer of the title compound as a yellow oil which solidifies upon standing (7.5 g, 78%). MS (ESI) m/z 223 (M−H)−.

Quelle