Reacción #56744

Ecuación de reacción

(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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter removal of the solvent in vacuum
2. 2
   Extracciónwas then extracted with ethyl acetate (4×300 mL)
3. 3
   SecadoThe combined organic layers were dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporate to dryness in vacuum
6. 6
   OtroThe crude brown oil thus obtained
7. 7
   Otrochromatographed on silica gel with 40% hexane/ethyl acetate as eluent

Procedimiento

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)−.

Fuente