Reaktion #73553

Reaktionsgleichung

1-Cyclopropylethynyl-4-methoxy-benzene Cyclopropylethyne

4-iodoanisole

triethylamine

→

1-cyclopropylethynyl-4-methoxy-benzene

Ausbeute 67.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe resulting precipitate was filtered
2. 2
   Waschenwashed with THF
3. 3
   SonstigeThe combined filtrate was evaporated to dryness
4. 4
   Sonstigethe residue was purified by column chromatography

Vorschrift

1-Cyclopropylethynyl-4-methoxy-benzene Cyclopropylethyne (15 g, 0.22 mol) was slowly added to a mixture of 4-iodoanisole (30 g, 0.13 mol), copper (I) iodide (1.2 g, 0.0063 mol), and triethylamine (30 g, 0.30 mol) in tetrahydrofuran (THF, 400 mL). After being stirred for 4 hours, the resulting precipitate was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by column chromatography to afford 1-cyclopropylethynyl-4-methoxy-benzene as a yellow oil (15 g, 0.087 mol, 67%). NMR (CDCl3) δ 7.31 (d, J=8.8 Hz, 2 H), 6.80 (d, J=8.8 Hz, 2H), 3.79 (s, 3H), 1.43 (m, 1H), 0.85 (m, 2H), 0.78 (m, 2H).

Quelle