반응 #309761

반응 방정식

potassium tert-butoxide

chloroacetonitrile

cyclopentanone

→

title compound

수율 68.3%

1-Oxa-spiro[2.4]heptane-2-carbonitrile

수율 68.3%

용매

t-butyl alcohol

tert-butyl alcohol

반응 조건

후처리

1. 1
   여과The mixture is filtered through diatomaceous earth
2. 2
   기타the solvent is removed
3. 3
   workup.ADDITIONthe residue is diluted with water
4. 4
   추출sodium dihydrogen phosphate solution and extracted with diethyl ether
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   여과filtered
7. 7
   기타the solvent is removed
8. 8
   기타The residue is purified by flash chromatography over silica gel

실험 절차

A 1 M solution of potassium tert-butoxide in tert-butyl alcohol (184.4 mL, 184.4 mmol) is added slowly to a solution of chloroacetonitrile (10.8 mL, 167.6 mmol) and cyclopentanone (15.0 mL, 167.6 mmol) in anhydrous t-butyl alcohol (33 mL). The reaction is stirred at room temperature for 16 h. The mixture is filtered through diatomaceous earth, the solvent is removed, and the residue is diluted with water. The mixture is neutralized with 30% aq.sodium dihydrogen phosphate solution and extracted with diethyl ether. The organic layers are combined, dried over anhydrous sodium sulfate, filtered, and the solvent is removed. The residue is purified by flash chromatography over silica gel to obtain 14.1 g of the title compound as a colourless oil. 1H NMR (CDCl3) δ (ppm): 3.46 (s, 1H), 1.65-2.20 (m, 8H).

출처