Pyridine → 1-Penten-3-yl Acetate

HRID 2399601Notes

Reaction equation

HRID 2399601 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH3:5].[C:6]([O:9]C(=O)C)(=[O:8])[CH3:7].N1C=CC=CC=1>CCOCC>[C:6]([O:9][CH:3]([CH2:4][CH3:5])[CH:2]=[CH2:1])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 80041-Pentene

Product 1

HCID 5303231-Penten-3-yl Acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The above pentene derivative (9.0 g, 25 mmols) and acetic anhydride (3.0 g, 30 mmols) are dissolved in ether (200 ml), followed by dropwise adding pyridine (5 ml), while stirring the solution under ice cooling, stirring the reaction liquid under ice cooling for one hour, elevating the temperature up to room temperature, stirring for 3 hours, pouring the reaction mixture into ice water after completion of the reaction, extracting with toluene (150 ml), washing the organic layer with water, drying over anhydrous magnesium sulfate and concentrating under reduced pressure to obtain 5-(4-(4-propylphenyl)phenyl)cyclohexyl)-3-acetyloxy-1-pentene pale yellow oil.

Workup

  1. stirringstirring
  2. customthe reaction liquid under ice cooling for one hour
  3. customup to room temperature
  4. stirringstirring for 3 hours
  5. customafter completion of the reaction
  6. extractionextracting with toluene (150 ml)
  7. washwashing the organic layer with water
  8. dry with materialdrying over anhydrous magnesium sulfate
  9. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-3c3ae2aeb27a498d8f9b2159de3a625a
Source dataset
uspto-grants-1995_09
Patent number
US05449810

Reaction notes

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