Ethyl ketone → 6,6-Diethyl-fulvene

HRID 270998Notes

Reaction equation

HRID 270998 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-4955c61d9d39472c91b9ab2814c69167
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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