Cyclohexylfulvene → (1-Methyl-1-cyclohexyl)cyclopentadiene

HRID 270987Notes

Reaction equation

HRID 270987 reaction equation
[CH:1]1([C:7]2[C:11](=C)[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:13][Li]>C1COCC1.CCOCC.O>[CH3:13][C:1]1([C:7]2[CH2:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 22327799CyclohexylfulveneHCID 178418348HCID 178418348, compound

Product 1

HCID 14688277(1-Methyl-1-cyclohexyl)cyclopentadieneYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.50 g (44.5 mmol) of cyclohexylfulvene in 60 ml of THF, 44.8 ml (51.1 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.72 g (16.76 mmol) of a colorless transparent liquid (yield: 38%) The analyzed values are given below.

Workup

  1. additionwas added
  2. washThe separated organic phase was washed with water
  3. dry with materiala saturated saline solution, then dried over magnesium sulfate
  4. filtrationfiltered
  5. customFrom the filtrate, the solvent was removed under reduced pressure
  6. customto obtain a liquid
  7. customThe liquid was isolated
  8. custompurified by column chromatography (silica gel, developing solvent: hexane)

Sources & evidence

ORD record
ord-f30bcdc8296743108352e821da840924
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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