Reaktion #10572

Reaktionsgleichung

trimethylsilyl acetylene

compound 1

1-Iodo-4-tetrahydropyranyloxybenzene

→

4-Tetrahydropyranyloxy-1-(trimethylsilylethynyl) benzene

Lösungsmittel

diisopropylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe salt formed during the reaction procedure
2. 2
   Filtrationwas filtered off
3. 3
   Waschenwashed well with ethyl acetate
4. 4
   SonstigeThe filtrate was evaporated to dryness and hydrolyzed with concentrated hydrochloric acid (5 ml), water (25 ml)
5. 5
   Sonstigecrushed ice (10 g)
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe combined organic paste was washed with brine
8. 8
   Trocknendried with MgSO4
9. 9
   SonstigeThe solvent was removed in vacuo
10. 10
    Sonstigethe residue was purified by column chromatography (petroleum ether-ethyl acetate=9:1)
11. 11
    Sonstigeto give a yellow oil of 2

Vorschrift

To a degassed solution of compound 1 (9.12 g, 30 mmol) in diisopropylamine (180 ml) under nitrogen, Pd(PPh3)2Cl2 (140 mg, 0.2 mmol) and CuI (78 mg, 0.4 mmol) were added. Then trimethylsilyl acetylene (3.3 g, 33 mmol) was added dropwise to this clear solution. The reaction mixture was stirred for 2 hours at room temperature. The salt formed during the reaction procedure was filtered off and washed well with ethyl acetate. The filtrate was evaporated to dryness and hydrolyzed with concentrated hydrochloric acid (5 ml), water (25 ml) and crushed ice (10 g), then extracted with ethyl acetate. The combined organic paste was washed with brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by column chromatography (petroleum ether-ethyl acetate=9:1) to give a yellow oil of 2. Yield 7.9 g (96%); δH(CDCl3; 300 MHz): 7.39(d, J=8.7, 2H, Ar—H, 6.97(d, J=8.6, 2H, Ar—H), 5.41(t, J=3.1, 1H, OCHO), 3.84(m, 1H, THP), 3.59(m, 1H, THP), 1.86˜1.61(m, 6H, THP), 0.23(s, 9H, 3 CH3).

Quelle