Ethyl ketone → 3-Tert-butyl-6,6-diethylfulvene

HRID 271021Notes

Reaction equation

HRID 271021 reaction equation
[C:1]([C:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14]C.C([Li])CCC.CCC(=O)CC>O.C1COCC1>[C:1]([C:5]1[CH:9]=[CH:8][C:7](=[C:12]([CH2:13][CH3:14])[CH2:11][CH3:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 7288Ethyl ketoneHCID 8058HexaneHCID 633714Tert-butylcyclopentadieneHCID 178418339Butyllithium

Product 1

HCID 178181433-Tert-butyl-6,6-diethylfulveneYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution of 1.53 g (13 mmol) of tert-butylcyclopentadiene, 9.0 ml (14 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 1.7 ml (16 mmol) of 3-pentanone was further added at −78° C., followed by stirring at room temperature for 2 days. To the reaction solution, water was added. The mixture was subjected to extraction with ether, then the solvent was distilled off, and the residue was subjected to column chromatography (silica gel, developing solvent: hexane) to obtain 1.50 g of a yellow liquid (yield: 63%) The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for 2 days
  2. extractionThe mixture was subjected to extraction with ether
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-492829f1ee094cf5bed84f145ae9dc33
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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