Réaction #48903

Équation de réaction

HCl

1-(2,3-dihydroxy-4-methoxyphenyl)ethanone

bromocyclopentane

potassium carbonate

→

1-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]ethanone

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températureto cool to rt
2. 2
   Extractionextracted with diethyl ether (250 mL×2)
3. 3
   AutreThe combined extracts were dried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Autrepurified by silica gel chromatography (1:0→17:3; hexanes:ethyl acetate)

Mode opératoire

A mixture of 1-(2,3-dihydroxy-4-methoxyphenyl)ethanone (10 g, 55 mmol), bromocyclopentane (6.0 mL, 56 mmol), potassium carbonate (15.5 g, 112 mmol), and anhydrous DMF (100 mL) was heated at 110° C. under N2 for 17 h and then allowed to cool to rt. The mixture was poured into 0.5N HCl (600 mL) and extracted with diethyl ether (250 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (1:0→17:3; hexanes:ethyl acetate) to give 1-[3-(cyclopentyloxy)-2-hydroxy-4-methoxyphenyl]ethanone: MS (ESI): 251.2.

Source