1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57814296, compound

HRID 1809136Notes

Reaction equation

HRID 1809136 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9](O)[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.P([N:34]=[N+:35]=[N-:36])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C1CCN2C(=NCCC2)CC1.ClC1C(Cl)=CC=CC=1C=CC1C=CN=CC=1>C1COCC1>[N:34]([CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[N+:35]=[N-:36]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 57814300HCID 57814300, compoundHCID 66925267HCID 66925267, compound

Product 1

HCID 57814296HCID 57814296, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)ethanol (7) (6.20 g, 23.2 mmol) in THF (100 mL) was added diphenyl phosphorazidate (6.00 mL, 27.8 mmol), and DBU (4.20 mL, 23.1 mmol) at 0° C. The mixture was stirred at room temperature overnight. The mixture was heated at 50° C. for 1.5 hour. The solvents were evaporated under reduced pressure. The residue was diluted with water, and extracted with ethyl acetate (3×). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. Silica gel was added to the filtrate, and the solvents were evaporated under reduce pressure. Purification by chromatography on silica gel (60% hexane, 40% ethyl acetate) gave a 4:1 mixture of products: 4-(2-azido-2-(2,3-dichlorophenyl)ethyl)pyridine (8) (4 parts, 3.82 g, 10.6 mmol, 46% yield), and 4-(2,3-dichlorostyryl)pyridine (9) (1 part).

Workup

  1. temperatureThe mixture was heated at 50° C. for 1.5 hour
  2. customThe solvents were evaporated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe pooled organic layer was dried over magnesium sulfate
  6. filtrationThe mixture was filtered
  7. additionSilica gel was added to the filtrate
  8. customthe solvents were evaporated
  9. customPurification by chromatography on silica gel (60% hexane, 40% ethyl acetate)
  10. customgave
  11. additiona 4:1 mixture of products

Sources & evidence

ORD record
ord-9d6cc257328043db8642443052b1d01e
Source dataset
uspto-grants-2013_01
Patent number
US08362022B2

Reaction notes

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