Acetone → 2-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-diene

HRID 495726Notes

Reaction equation

HRID 495726 reaction equation
[C:1]([C:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:10][C:11]([CH3:13])=O.CO.N1CCCC1>C(O)(=O)C.CCOCC.O>[C:1]([C:5]1[CH:9]=[CH:8][C:7](=[C:11]([CH3:13])[CH3:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 31268PyrrolidineHCID 633714Tert-butylcyclopentadiene

Product 1

HCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-dieneYield 90.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixed solution of 1.40 g (11 mmol) of tert-butylcyclopentadiene, 8.4 ml (114 mmol) of acetone and 20 ml of methanol, 9.5 ml (114 mmol) of pyrrolidine was added with ice cooling, followed by stirring at room temperature for one night. To the reaction solution, 50 ml of water, 100 ml of ether and 3 ml of acetic acid were added with ice cooling. The separated organic phase was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was subjected to column chromatography (silica gel, developing solvent: hexane) to obtain 1.62 g of a yellow liquid (yield: 88%).

Workup

  1. washThe separated organic phase was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-fe5bfe36c43045fc8249f5c4ac3cd36a
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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