Reaktion #1993394

Reaktionsgleichung

hydrochloric acid

iodohexyl chromanone

rac.-[[3,4-dihydro-2-(6-iodohexyl)-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid methyl ester

2,4-dihydroxy-3-propylacetophenone

potassium bicarbonate

→

rac-[[2-[6-(4-acetyl-3-hydroxy-2-propylphenoxy)-hexyl]-3,4-dihydro-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid methyl ester

Ausbeute 83.4%

Lösungsmittel

N,N-dimethylformamide

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed
2. 2
   TemperaturThe resulting mixtures was cooled
3. 3
   Extraktionextracted 3 times with ether
4. 4
   WaschenThe combined ether extracts were washed with saturated aqueous sodium bicarbonate, water, and brine
5. 5
   Trocknendried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigegiving 1.5 of an oil
9. 9
   SonstigeThis material was chromatographed on 45 g of silica gel
10. 10
    WaschenElution with 2:1 hexane-ethyl acetate

Vorschrift

A mixture of 1.25 g of the iodohexyl chromanone product from Example 4, 0.49 g of 2,4-dihydroxy-3-propylacetophenone, 0.841 g of anhydrous potassium bicarbonate, 25 ml of acetone, and 12 ml of N,N-dimethylformamide was refluxed and stirred for 6 hours. The resulting mixtures was cooled, poured into cold 1N hydrochloric acid, and extracted 3 times with ether. The combined ether extracts were washed with saturated aqueous sodium bicarbonate, water, and brine, then dried (magnesium sulfate), filtered and concentrated in vacuo giving 1.5 of an oil. This material was chromatographed on 45 g of silica gel. Elution with 2:1 hexane-ethyl acetate afforded 1.18 g (83.4%) of rac-[[2-[6-(4-acetyl-3-hydroxy-2-propylphenoxy)-hexyl]-3,4-dihydro-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid methyl ester as a colorless oil.

Quelle