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

HRID 270985Notes

Reaction equation

HRID 270985 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-cb5d1c826d7e47cb80af0dfe7127fa08
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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