Reacción #10572

Ecuación de reacción

trimethylsilyl acetylene

compound 1

1-Iodo-4-tetrahydropyranyloxybenzene

→

4-Tetrahydropyranyloxy-1-(trimethylsilylethynyl) benzene

Disolventes

diisopropylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe salt formed during the reaction procedure
2. 2
   Filtraciónwas filtered off
3. 3
   Lavadowashed well with ethyl acetate
4. 4
   OtroThe filtrate was evaporated to dryness and hydrolyzed with concentrated hydrochloric acid (5 ml), water (25 ml)
5. 5
   Otrocrushed ice (10 g)
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   LavadoThe combined organic paste was washed with brine
8. 8
   Secadodried with MgSO4
9. 9
   OtroThe solvent was removed in vacuo
10. 10
    Otrothe residue was purified by column chromatography (petroleum ether-ethyl acetate=9:1)
11. 11
    Otroto give a yellow oil of 2

Procedimiento

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).

Fuente