반응 #466902

반응 방정식

trimethylsilyl cyanide

phosphorous oxychloride

3-cyano-3-(cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one

18-crown-6

potassium cyanide

toluene

→

oil

수율 42.0%

5-(3-cyclopentyloxy-4-methoxyphenyl)cyclohex-1-ene-1,5-dicarbonitrile

수율 42.0%

용매

Pyridine

반응 조건

후처리

1. 1
   온도the solution was refluxed for 40 h
2. 2
   기타After quenching with ice
3. 3
   추출the reaction was extracted three times with methylene chloride
4. 4
   세척the extract was washed with sodium bicarbonate, 10% hydrochloric acid and water
5. 5
   건조was dried (magnesium sulfate)
6. 6
   기타the solvent was evaporated
7. 7
   기타Purification by flash chromatography
8. 8
   세척eluting with 1:4 ethyl acetate/hexanes

실험 절차

A suspension of 3-cyano-3-(cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.63 g, 2.0 mmol), 18-crown-6 (0.006 g, 0.1 mmol) and potassium cyanide (0.006 g, 0.1 mmol) in dry toluene (2 mL) at room temperature under an argon atmosphere was treated dropwise with trimethylsilyl cyanide (0.32 mL, 2.4 mmol) and the mixture was stirred for 2.5 h. Pyridine (4 mL) and phosphorous oxychloride (0.5 mL, 5.0 mmol) were added, and the solution was refluxed for 40 h. After quenching with ice, the reaction was extracted three times with methylene chloride, the extract was washed with sodium bicarbonate, 10% hydrochloric acid and water, was dried (magnesium sulfate) and the solvent was evaporated. Purification by flash chromatography, eluting with 1:4 ethyl acetate/hexanes, provided a pale yellow oil (0.3 g, 42%). Anal. (C20H22N2O2.3/8H2O) calcd: C, 72.98; H, 6.97; N, 8.51; found: C, 72.85; H, 6.80; N, 8.56; Rf=0.13 (4:1 hexanes/ethyl acetate).

출처