Water → 1-(2-pyridyl)cyclopentene

HRID 1581902Notes

Reaction equation

HRID 1581902 reaction equation
O[CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.O>C(Cl)Cl>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:3]1[CH2:4][CH2:5][CH2:6][CH:2]=1

Participants

4

Reactant 2

HCID 962WaterHCID 13416605HCID 13416605, compound

Product 1

HCID 122178021-(2-pyridyl)cyclopenteneYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
170 °C

Procedure

In an autoclave, 60.0 g (368 mM) of 1-hydroxy-2-(2-pyridyl)cyclopentane was placed and stirred for 60 hours at 170° C., followed by cooling, addition of water and extraction with methylene chloride. The organic layer was dried with anhydrous sodium sulfate, followed by distilling-off of the solvent under reduced pressure and then purification by silica gel column chromatography (eluent: hexane/ethyl acetate=8/1) to obtain 28.0 g of liquid 1-(2-pyridyl)cyclopentene (Yield: 52.5%).

Workup

  1. temperatureby cooling
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. custompurification by silica gel column chromatography (eluent: hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-88c005ed4bf74721916cefb4506249f3
Source dataset
uspto-grants-2004_05
Patent number
US06733905B2

Reaction notes

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