Toluene → HCID 18368388, compound

HRID 379720Notes

Reaction equation

HRID 379720 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2OC2CCCC2)[CH2:8][CH2:7][CH2:6][C:5](=O)[CH2:4]1)#[N:2].C1[O:41][CH2:40][CH2:39]OCCOCCOCCOCCOC1.[C-]#N.[K+].C[Si]([C:49]#[N:50])(C)C.P(Cl)(Cl)(Cl)=O.[C:56]1(C)[CH:61]=CC=C[CH:57]=1>N1C=CC=CC=1>[CH:40]1([O:41][C:14]2[CH:15]=[C:10]([C:3]3([C:1]#[N:2])[CH2:4][C:5]([C:49]#[N:50])=[CH:6][CH2:7][CH2:8]3)[CH:11]=[CH:12][C:13]=2[O:16][CH3:17])[CH2:39][CH2:61][CH2:56][CH2:57]1

Participants

8

Reactant 6

HCID 1140TolueneHCID 9032Potassium CyanideHCID 24813Phosphorus oxychlorideHCID 2855718-Crown-6HCID 82115Trimethylsilyl cyanideHCID 18368410HCID 18368410, compound

Product 1

HCID 18368388HCID 18368388, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Workup

  1. temperaturethe solution was refluxed for 40 h
  2. customAfter quenching with ice
  3. extractionthe reaction was extracted three times with methylene chloride
  4. washthe extract was washed with sodium bicarbonate, 10% hydrochloric acid and water
  5. dry with materialwas dried (magnesium sulfate)
  6. customthe solvent was evaporated
  7. customPurification by flash chromatography
  8. washeluting with 1:4 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-76e2d5edbebe4ea09765bbb0fe020ab5
Source dataset
uspto-grants-2001_10
Patent number
US06300372B1

Reaction notes

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