Reaktion #10573

Reaktionsgleichung

2

4-Tetrahydropyranyloxy-1-(trimethylsilylethynyl) benzene

→

4-Tetrahydropyranyloxyphenylacetylene

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed under reduced pressure on a rotary evaporator
2. 2
   SonstigeThe residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1)
3. 3
   Sonstigeto give a pale yellow crystals of 3

Vorschrift

(9.3 g, 160 mmol) was added to a stirred solution of 2 (22.6 g, 80 mmol) in MeOH (150 ml). The reaction mixture was stirred at room temperature for about 4 hours. After the reaction finished (GC shows no starting material remaining), the solvent was removed under reduced pressure on a rotary evaporator. The residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1) to give a pale yellow crystals of 3. Yield 15.7 g(97%); mp 65° C., δH(CDCl3; 300 MHz): 7.42(d, J=8.7, 2H, Ar—H), 7.00(d, J=8.7, 2H, Ar—H), 5.43(t, J=3.2, 1H, OCHO), 3.87(m, 1H, THP, 3.60(m, 1H, THP), 2.99(s, 1H, C═C—H), 1.96˜1.56(m, 6H, THP).

Quelle