반응 #10572

반응 방정식

trimethylsilyl acetylene

compound 1

1-Iodo-4-tetrahydropyranyloxybenzene

→

4-Tetrahydropyranyloxy-1-(trimethylsilylethynyl) benzene

용매

diisopropylamine

반응 조건

후처리

1. 1
   기타The salt formed during the reaction procedure
2. 2
   여과was filtered off
3. 3
   세척washed well with ethyl acetate
4. 4
   기타The filtrate was evaporated to dryness and hydrolyzed with concentrated hydrochloric acid (5 ml), water (25 ml)
5. 5
   기타crushed ice (10 g)
6. 6
   추출extracted with ethyl acetate
7. 7
   세척The combined organic paste was washed with brine
8. 8
   건조dried with MgSO4
9. 9
   기타The solvent was removed in vacuo
10. 10
    기타the residue was purified by column chromatography (petroleum ether-ethyl acetate=9:1)
11. 11
    기타to give a yellow oil of 2

실험 절차

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).

출처