Reaktion #344634

Reaktionsgleichung

nitropropane

sodiummethoxide

acetylchloride

2-ethynylpyridine

→

3-(3-ethyl-5-isoxazolyl)pyridine

Lösungsmittel

Water

dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe solution extracted with 3×30 ml ethylacetate
2. 2
   TrocknenThe organic phase was dried over magnesiumsulphate
3. 3
   Einengenconcentrated in vacuo

Vorschrift

0.45 g (5 mmole) nitropropane and 5 ml 1N (5 mmole) sodiummethoxide was dissolved in dry dimethylacetamide (25 ml). To this solution 0.39 g (5 mmole) acetylchloride and 0.51 g (5 mmole) 2-ethynylpyridine was added. The reaction mixture was stirred overnight at room temperature. Water (150 ml) was added, and the solution extracted with 3×30 ml ethylacetate. The organic phase was dried over magnesiumsulphate and concentrated in vacuo giving 3-(3-ethyl-5-isoxazolyl)pyridine in a 500 mg yield. This compound was quartarnized with methyliodide and reduced with sodiumborohydride as described above giving the title compound in a 170 mg yield. M.p. 169°-170° C.

Quelle