Cyclopentadiene → 6-Methyl-6-isobutylfulvene

HRID 271002Notes

Reaction equation

HRID 271002 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[CH2:6]([C:10]([CH3:12])=O)[CH:7]([CH3:9])[CH3:8].N1CCCC1>CO.CCOCC.O>[CH3:12][C:10]([CH2:6][CH:7]([CH3:9])[CH3:8])=[C:2]1[CH:1]=[CH:5][CH:4]=[CH:3]1

Participants

7

Reactant 3

HCID 7612CyclopentadieneHCID 7909Methyl Isobutyl KetoneHCID 31268Pyrrolidine

Product 1

HCID 5626186-Methyl-6-isobutylfulveneYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10.00 g (151.3 mmol) of cyclopentadiene in 30 ml of methanol, 18.9 ml (151.1 mmol) of methyl isobutyl ketone and 12.8 ml (153.3 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 (83-88° C./10 mmHg) to obtain 15.80 g (106.58 mmol) of a yellow liquid (yield: 71%). 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 (83-88° C./10 mmHg)

Sources & evidence

ORD record
ord-ee6b784eb9e544e29ea46b6d56566c84
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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