Cyclopentadiene → 5-(Pentan-2-ylidene)cyclopenta-1,3-diene

HRID 495748Notes

Reaction equation

HRID 495748 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[CH2:6]([C:9]([CH3:11])=O)[CH2:7][CH3:8].N1CCCC1>CO.CCOCC.O>[CH3:8][C:7]([CH2:6][CH2:9][CH3:11])=[C:2]1[CH:1]=[CH:5][CH:4]=[CH:3]1

Participants

7

Reactant 3

HCID 7612CyclopentadieneHCID 78952-PentanoneHCID 31268Pyrrolidine

Product 1

HCID 129395315-(Pentan-2-ylidene)cyclopenta-1,3-dieneYield 61%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10.00 g (151.3 mmol) of cyclo pentadiene in 40 ml of methanol, 18.6 ml (174.2 mmol) of methyl propyl ketone and 4.5 ml (54.7 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (70° C./1 mmHg) to obtain 12.30 g (91.64 mmol) of a yellow liquid (yield: 61%). The analyzed values are given below.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materiala saturated saline solution, then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. distillationThe liquid was subjected to vacuum distillation (70° C./1 mmHg)

Sources & evidence

ORD record
ord-8b87efa02d214fadb553874996037d50
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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