Toluene → HCID 18599124, compound

HRID 485931Notes

Reaction equation

HRID 485931 reaction equation
C1(C)C=CC=CC=1.[OH:8][N:9]=[C:10]1[CH2:18][C@@H:17]2[C@@H:12]([CH2:13][CH:14]=[CH:15][CH2:16]2)[CH2:11]1.[H-].[Na+].Cl[CH2:22][CH2:23][CH2:24][C:25]#[N:26]>O>[C:25]([CH2:24][CH2:23][CH2:22][O:8][N:9]=[C:10]1[CH2:11][C@@H:12]2[C@@H:17]([CH2:16][CH:15]=[CH:14][CH2:13]2)[CH2:18]1)#[N:26]

Participants

6

Reactant 4

HCID 1140TolueneHCID 123364-ChlorobutyronitrileHCID 24758Sodium hydrideHCID 18599125HCID 18599125, compound

Product 1

HCID 18599124HCID 18599124, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a toluene solution (20 ml) of 8-hydroxyimino-cis-bicyclo[4,3,0]nona-3-ene (1 g), was added sodium hydride (50% mineral oil dispersion, 330 mg), and the mixture was stirred for 0.5 hr at room temperature. After addition of γ-chlorobutyronitrile (5 g) to the mixture, stirring was continued for 2 hr. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over Na2SO4 and concentrated to give an oil. This material was chromatographed on silica gel to give 8-(3'-cyanopropoxy)imino-cis-bicyclo[4,3,0]nona-3-ene as an oil.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hr
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give an oil
  9. customThis material was chromatographed on silica gel

Sources & evidence

ORD record
ord-3d3bf6b09f7541618236ef1e5ebbca3a
Source dataset
uspto-grants-1985_08
Patent number
US04537989

Reaction notes

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