反应详情

温度

-20 °C

To 7.2 g of trimethylsilylacetylene dissolved in 110 ml of THF and cooled to -20° C. was added 46.2 ml of 1.55M n-butyl lithium in hexane. The mixture was allowed to come to room temperature for 15 minutes, recooled to -20° C., and treated dropwise with 5.3 g of phenoxyacetaldehyde (II) in THF. After the addition was complete, the reaction mixture was stirred at 0° C. for 4 hours. The reaction mixture was then poured into a mixture of ether:hexane (1:1) over 0.5N HCl and shaken. The organic layer was separated, washed 3 times with H2O, dried (Na2SO4), and evaporated to dryness. The residue was chromatographed on a column of silica gel that was eluted with 30% ethyl acetate in hexane to yield 3.8 g of 1-phenoxy-4-trimethylsilylbut-3-yn-2-ol (III).

1. customrecooled to -20° C.
2. additionAfter the addition
3. stirringshaken
4. customThe organic layer was separated
5. washwashed 3 times with H2O
6. dry with materialdried (Na2SO4)
7. customevaporated to dryness
8. customThe residue was chromatographed on a column of silica gel that
9. washwas eluted with 30% ethyl acetate in hexane