反応 #49734

反応方程式

sodium chloride

n-butyllithium

[2-chloro-4-(methylsulphenyl)phenyl]acetylene

cyclopropanecarbonyl chloride

→

1-[2-chloro-4-(methylsulphenyl)phenyl]-3-cyclopropylprop-1-yn-3-one

溶媒

hexane

THF

反応条件

後処理

1. 1
   温度while maintaining the temperature below -70° C
2. 2
   抽出The aqueous layer was extracted with ether
3. 3
   乾燥dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   その他The filtrate was evaporated to dryness
6. 6
   workup.DISSOLUTIONthe residue was dissolved in methanol
7. 7
   温度heated
8. 8
   温度at reflux for 5 minutes
9. 9
   workup.ADDITIONToluene was added
10. 10
    その他the mixture was evaporated to dryness
11. 11
    その他The residue was purified by chromatography
12. 12
    洗浄eluted with a mixture of hexane and ether

実験手順

A solution of n-butyllithium in hexane (4.4 ml) was added to a stirred solution of [2-chloro-4-(methylsulphenyl)phenyl]acetylene (2.0 g) in THF while maintaining the temperature below -70° C. The mixture was stirred for 5 minutes and cyclopropanecarbonyl chloride (2.4 g) was added. The mixture was warmed to room temperature and poured onto aqueous sodium chloride solution. The aqueous layer was extracted with ether and combined organic layers dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was dissolved in methanol and heated at reflux for 5 minutes. Toluene was added and the mixture was evaporated to dryness. The residue was purified by chromatography eluted with a mixture of hexane and ether to give 1-[2-chloro-4-(methylsulphenyl)phenyl]-3-cyclopropylprop-1-yn-3-one as yellow oil which crystallized on standing, m.p. 46°-50° C. [2-Chloro-4-(methylsulphenyl)phenyl]acetylene was prepared by the reaction of 1-bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetylene with n-butyllithium and wet zinc chloride in THF at -70° C.

出典