반응 #8319

반응 방정식

citric acid

6-trifluoromethyl-pyridine-2-carbothioic acid S-(4-chloro-phenyl) ester

4-fluorophenylacetonitrile

potassium bis(trimethylsilyl)amide

→

2-(4-fluoro-phenyl)-3-oxo-3-(6-trifluoromethyl-pyridin-2-yl)-propionitrile

수율 66.0%

용매

methylene chloride

tetrahydrofuran

반응 조건

후처리

1. 1
   기타to warn to room temperature
2. 2
   온도then warmed
3. 3
   온도to reflux for 10 min, at which time the reaction
4. 4
   온도to cool
5. 5
   추출extracted into methylene chloride
6. 6
   건조The methylene chloride solution is dried over magnesium sulfate
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue is purified on a silica gel cartridge
9. 9
   기타prepared with hexane
10. 10
    세척then eluted with methylene chloride

실험 절차

A solution of 4-fluorophenylacetonitrile (0.12 mL, 1.0 mmol) in dry tetrahydrofuran (2 mL) is treated dropwise with potassium bis(trimethylsilyl)amide (0.5 M toluene, 3.0 mL, 1.5 mmol) at 0° C. under an atmosphere of nitrogen. The mixture is stirred 10 min then 6-trifluoromethyl-pyridine-2-carbothioic acid S-(4-chloro-phenyl) ester is added all at once. The mixture is allowed to warn to room temperature then warmed to reflux for 10 min, at which time the reaction is complete by TLC (methylene chloride). The mixture is allowed to cool then poured into 10% citric acid and extracted into methylene chloride. The methylene chloride solution is dried over magnesium sulfate and concentrated in vacuo. The residue is purified on a silica gel cartridge prepared with hexane then eluted with methylene chloride to yield 204 mg (66%) 2-(4-fluoro-phenyl)-3-oxo-3-(6-trifluoromethyl-pyridin-2-yl)-propionitrile. MS ES− m/z 307 (M−1).

출처