Triethylamine → 6-Undecyl-2-pyridinecarbonitrile

HRID 1587710Notes

Reaction equation

HRID 1587710 reaction equation
[CH2:1]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:19]([N:21](CC)CC)C>C(#N)C>[C:19]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[N:13]=1)#[N:21]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54199337HCID 54199337, compound

Product 1

HCID 197561096-Undecyl-2-pyridinecarbonitrileYield 52.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 10.0 g (40 mmol) of 2-n-undecylpyridine N-oxide and 8.10 g (80 mmol) of triethylamine dissolved in 40 ml of acetonitrile was dropwise added 15.8 g of trimethylsilylanilide while stirring at room temperature. After the dropwise addition, the mixture was refluxed for 67 hours, concentrated under a reduced pressure, followed by separation by silica gel column chromatography (ethyl acetate:hexane=1:9) to give 5.40 g of an oily product (yield 52.1%).

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe mixture was refluxed for 67 hours
  3. concentrationconcentrated under a reduced pressure
  4. customfollowed by separation by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-b34c1bdea02d4619ae04e6279271403e
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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