반응 #814370

반응 방정식

sodium hydride

8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane

trimethylsilylacetylene

→

8-trimethylsilylethynyl-1,4-dioxaspiro[4.5]decane

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   workup.STIRRINGthe reaction mixture is stirred at ambient temperature for about one hour
3. 3
   workup.ADDITIONUpon completion of addition
4. 4
   온도to warm to ambient temperature where it
5. 5
   workup.STIRRINGis stirred during about 18 hours
6. 6
   농축After this time the reaction mixture is concentrated under reduced pressure to a residue
7. 7
   workup.STIRRINGThe residue is stirred in water
8. 8
   추출the mixture is extracted with three 50 mL portions of diethyl ether
9. 9
   세척The combined extracts are washed with water
10. 10
    건조dried with magnesium sulfate
11. 11
    여과The mixture is filtered
12. 12
    농축the filtrate is concentrated under reduced pressure

실험 절차

Under a nitrogen atmosphere, a mixture of 3.2 grams (0.08 mole) of sodium hydride (60% in mineral oil) in 25 mL of tetrahydrofuran is stirred, and a solution of 7.9 grams (0.08 mole) of trimethylsilylacetylene in 15 mL of tetrahydrofuran is added dropwise. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about one hour. The reaction mixture is then cooled to 0° C., and a solution of 18.9 grams (0.08 mole) of 8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane in 25 mL of tetrahydrofuran is added dropwise. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred during about 18 hours. After this time the reaction mixture is concentrated under reduced pressure to a residue. The residue is stirred in water, and the mixture is extracted with three 50 mL portions of diethyl ether. The combined extracts are washed with water and dried with magnesium sulfate. The mixture is filtered, and the filtrate is concentrated under reduced pressure, yielding 8-trimethylsilylethynyl-1,4-dioxaspiro[4.5]decane.

출처