Water → (4-Methoxymethoxy-phenylethynyl)-trimethylsilane

A solution of 4-(2,2-dibromoethenyl)phenol methoxymethyl ether (16.56 g) in THF (350 ml) was cooled to -78° C., to which was added dropwise, under argon atmosphere, a 1.6M n-butyl lithium hexane solution (70 ml). The mixture was stirred for one hour under the same conditions, which was then warmed and stirred for one hour at room temperature. The reaction mixture was cooled with ice, to which was added dropwise trimethylchlorosilane (7.2 ml). The mixture was then stirred for 3 hours while warming up to room temperature, to which was added water to quench the reaction, followed by extraction with ethyl acetate. The organic layer was washed (a saturated aqueous saline solution) and dried (anhydrous magnesium sulfate), then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 4-(2-trimethylsilylethynyl)phenol methoxymethyl ether (10.76 g) (Compound B-26). The physical properties are shown in Table 8.

1. additionwas added dropwise, under argon atmosphere
2. temperaturewas then warmed
3. stirringstirred for one hour at room temperature
4. temperatureThe reaction mixture was cooled with ice, to which
5. stirringThe mixture was then stirred for 3 hours
6. customto quench
7. customthe reaction
8. extractionfollowed by extraction with ethyl acetate
9. washThe organic layer was washed (a saturated aqueous saline solution) and
10. dry with materialdried (anhydrous magnesium sulfate)
11. distillationthe solvent was distilled off under reduced pressure
12. customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

ORD-Eintrag

ord-6b044bd90cf64d54978473a34cffc4cc

Quelldatensatz

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05716971