反应 #1074073

反应方程式

tetrabutylammonium fluoride

3-(3-bromophenoxy)tetrahydropyran

triphenylphosphine

trimethylsilylacetylene

→

3-(3-ethynylphenoxy)tetrahydropyran

溶剂

THF

water

triethylamine

反应条件

后处理

1. 1
   其他The precipitated ammonium salts was removed by filtration
2. 2
   其他the filtrate was evaporated to dryness
3. 3
   其他This affords a yellowish oil which
4. 4
   温度cooled at 0° C.
5. 5
   workup.STIRRINGAfter stirring for 30 min the reaction
6. 6
   过滤the obtained brownish solution was filtered over a short silica-gel column
7. 7
   浓缩concentrated
8. 8
   其他to yield a brownish residue, which
9. 9
   其他was chromatographed on silica-gel column

实验过程

To a well degassed solution of 3-(3-bromophenoxy)tetrahydropyran (5.14 g), triphenylphosphine (204 mg), copper(I) iodide (38 mg) and bis(triphenylphosphine)palladium(II) dichloride (3.93 g) in triethylamine (40 ml), maintained under argon atmosphere, trimethylsilylacetylene is added and the mixture is stirred at 85° C. for 3 h. The precipitated ammonium salts was removed by filtration and the filtrate was evaporated to dryness. This affords a yellowish oil which is dissolved in 30 ml of THF containing 3 ml of water, then cooled at 0° C. and treated by dropwise addition of 5 ml of tetrabutylammonium fluoride (1M in THF). After stirring for 30 min the reaction was complete and the obtained brownish solution was filtered over a short silica-gel column and concentrated to yield a brownish residue, which was chromatographed on silica-gel column affording 3-(3-ethynylphenoxy)tetrahydropyran as yellowish crystals.

来源