반응 #216500

반응 방정식

water

n-butyllithium

trimethylsilylacetylene

1-chloro-3-iodopropane

→

5-Chloro-1-trimethylsilylpent-1-yne

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도to warm to 20°
2. 2
   workup.STIRRINGstirred for 18 hours
3. 3
   추출the aqueous mixture was extracted with diethyl ether
4. 4
   세척The ethereal extracts were washed with water
5. 5
   건조dried over anhydrous magnesium sulphate
6. 6
   기타The solvent was removed in vacuo
7. 7
   workup.DISTILLATIONthe residue distilled

실험 절차

A solution of trimethylsilylacetylene (12.0 g., Aldrich) in dry tetrahydrofuran (100 ml.) was stirred at 0°, under a current of nitrogen and n-butyllithium (76.5 ml. of 1.6M solution in hexane) was added dropwise. The solution was stirred for 30 minutes and a solution of 1-chloro-3-iodopropane (25.0 g.) in dry tetrahydrofuran (75 ml.) was added. The reaction mixture was allowed to warm to 20° and stirred for 18 hours. The mixture was poured into water and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue distilled. 5-Chloro-1-trimethylsilylpent-1-yne was obtained as a colourless oil (12.7 g., b.p. 67°-72°, 15 mm. Hg.).

출처