반응 #56744

반응 방정식

(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

용매

DMF

반응 조건

후처리

1. 1
   기타After removal of the solvent in vacuum
2. 2
   추출was then extracted with ethyl acetate (4×300 mL)
3. 3
   건조The combined organic layers were dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   기타evaporate to dryness in vacuum
6. 6
   기타The crude brown oil thus obtained
7. 7
   기타chromatographed on silica gel with 40% hexane/ethyl acetate as eluent

실험 절차

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)−.

출처