Water → (1-Ethyl-1-methylpropyl)cyclopentadiene

HRID 495740Notes

Reaction equation

HRID 495740 reaction equation
[CH2:1]([C:3]([CH2:9][CH3:10])=[C:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[CH3:2].[CH3:11][Li].O>CCOCC>[CH2:1]([C:3]([C:4]1[CH2:8][CH:7]=[CH:6][CH:5]=1)([CH3:11])[CH2:9][CH3:10])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 112057726,6-Diethyl-fulveneHCID 178418348HCID 178418348, compound

Product 1

HCID 14612254(1-Ethyl-1-methylpropyl)cyclopentadieneYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 8.00 g (59.6 mmol) of 6,6-diethylfulvene in 35 ml of ether, 60.0 ml (68.4 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. Then, 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 subjected to vacuum distillation (92° C./40 mmHg) to obtain 5.50 g (36.6 mmol) of a light yellow liquid (yield: 61%). The analyzed values are given below.

Workup

  1. washThe separated organic phase was washed with water
  2. dry with materiala saturated saline solution, then dried over magnesium sulfate
  3. filtrationfiltered
  4. customFrom the filtrate, the solvent was removed under reduced pressure
  5. customto obtain a liquid
  6. distillationThe liquid was subjected to vacuum distillation (92° C./40 mmHg)

Sources & evidence

ORD record
ord-0e20b6d132b04904a9eda6e1a0483d6b
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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