반응 #346092

반응 방정식

2-thenonitrile

tetrahydrofuran

tetrahydrofuran

2-(3-bromo-o-tolyl)-2-methyl-1,3-dioxolane

magnesium

ammonium chloride

→

2'-methyl-3'-(2-thenoyl)acetophenone

반응 조건

후처리

1. 1
   온도refluxing Grignard-complex
2. 2
   기타previously prepared
3. 3
   workup.STIRRINGUpon completion, stirring
4. 4
   온도at reflux
5. 5
   workup.WAITto stirr overnight at room temperature
6. 6
   기타the temperature below 20° C
7. 7
   추출The product is extracted with 1200 parts of ether
8. 8
   세척The extract is washed three times with 300 parts of water
9. 9
   기타upon saturation of the ether-phase with gaseous hydrogen chloride, the ketimine-compound is separated as an oil
10. 10
    기타The ether is decanted
11. 11
    workup.STIRRINGthe oil is stirred
12. 12
    온도refluxed for 3 hours in 500 parts of a 6N hydrochloric acid solution
13. 13
    온도After cooling
14. 14
    추출the product is extracted with chloroform (2 × 225 parts)
15. 15
    기타The extract is dried
16. 16
    기타evaporated
17. 17
    workup.DISTILLATIONThe residue is distilled twice

실험 절차

To a stirred and refluxing Grignard-complex, previously prepared starting from 72 parts of 2-(3-bromo-o-tolyl)-2-methyl-1,3-dioxolane, 6.8 parts of magnesium and 180 parts of dry tetrahydrofuran, is added dropwise a solution of 30.6 parts of 2-thenonitrile in 90 parts of dry tetrahydrofuran. Upon completion, stirring at reflux is continued for 2 hours. The reaction mixture is allowed to stirr overnight at room temperature. After cooling to 0° C, the mixture is decomposed by the addition of 200 parts of a saturated ammonium chloride solution while keeping the temperature below 20° C. The product is extracted with 1200 parts of ether. The extract is washed three times with 300 parts of water and upon saturation of the ether-phase with gaseous hydrogen chloride, the ketimine-compound is separated as an oil. The ether is decanted and the oil is stirred and refluxed for 3 hours in 500 parts of a 6N hydrochloric acid solution. After cooling, the product is extracted with chloroform (2 × 225 parts). The extract is dried and evaporated. The residue is distilled twice, yielding 2'-methyl-3'-(2-thenoyl)acetophenone; bp. 185°-190° C at 0.4 mm. pressure.

출처