Tetrahydrofuran → HCID 53851550, compound

HRID 2414076Notes

Reaction equation

HRID 2414076 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([CH2:10][CH3:11])[C:8]#[N:9].[C:12]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1.O1[CH2:24][CH2:23][CH2:22]C1>>[C:18]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH2:10][CH2:11][N:1]([CH:2]([CH3:7])[CH3:3])[CH:23]([CH3:24])[CH3:22])[C:8]#[N:9])#[N:19]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 746191-CyclohexenecarbonitrileHCID 125205092-(Pyridin-2-yl)butanenitrile

Product 1

HCID 53851550HCID 53851550, compound

Conditions

Temperature
20 °C

Procedure

To the solution of 36.75 g of 4-diisopropylamino 2-(2-pyridyl butyronitrile (Example 1a) in 300 ml of tetrahydrofuran are added at ambient temperature 71.7 g of Triton B then 15.9 g of 1-cyclohexene carbonitrile dissolved in 100 ml of tetrahydrofuran. The mixture is left for one night with stirring at ambient temperature (about 20° C.), then the solvent is evaporated to dryness. The residue is taken up in water and extracted 3 times with ether. The solvent is evaporated and the residue is chromatographed over a column of alumina. By eluting with a pentane-ethyl acetate (80-20) vol/vol mixture, 20 g of the expected product are obtained, used as such for cyclization.

Workup

  1. waitThe mixture is left for one night
  2. customthe solvent is evaporated to dryness
  3. extractionextracted 3 times with ether
  4. customThe solvent is evaporated
  5. customthe residue is chromatographed over a column of alumina
  6. washBy eluting with a pentane-ethyl acetate (80-20) vol/vol mixture, 20 g of the expected product
  7. customare obtained

Sources & evidence

ORD record
ord-58724b3a0e5744759aaf9925841585f0
Source dataset
uspto-grants-1988_01
Patent number
US04721710

Reaction notes

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