Water → (1,1-Dimethylpropyl)cyclopentadiene

HRID 270995Notes

Reaction equation

HRID 270995 reaction equation
[CH3:1][C:2]([CH2:8][CH3:9])=[C:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH3:10][Li].O>CCOCC>[CH3:1][C:2]([C:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1)([CH3:10])[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 5707046-Methyl-6-ethylfulveneHCID 178418348HCID 178418348, compound

Product 1

HCID 12779334(1,1-Dimethylpropyl)cyclopentadieneYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 8.00 g (66.6 mmol) of 6-methyl-6-ethylfulvene in 40 ml of ether, 66.0 ml (75.2 mmol) of an ether solution of methyllithium was dropwise added in an 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 (165° C./270 mmHg) to obtain 8.40 g (61.66 mmol) of a light yellow liquid (yield: 93%) 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 (165° C./270 mmHg)

Sources & evidence

ORD record
ord-2aaf108bc2dd4e90ad3f20e1d6b73431
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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