Ethyl ketone → 6,6-Diethyl-fulvene

HRID 495739Notes

Reaction equation

HRID 495739 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[CH2:6]([C:8]([CH2:10][CH3:11])=O)[CH3:7].N1CCCC1>CO.CCOCC.O>[CH2:6]([C:8]([CH2:10][CH3:11])=[C:2]1[CH:1]=[CH:5][CH:4]=[CH:3]1)[CH3:7]

Participants

7

Reactant 3

HCID 7288Ethyl ketoneHCID 7612CyclopentadieneHCID 31268Pyrrolidine

Product 1

HCID 112057726,6-Diethyl-fulveneYield 82%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 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 (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). 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 (78-83° C./4 mmHg)

Sources & evidence

ORD record
ord-12228387294f4505ad539be9e9cce085
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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