5-(Pentan-2-ylidene)cyclopenta-1,3-diene → HCID 12779343, compound

HRID 271009Notes

Reaction equation

HRID 271009 reaction equation
[CH3:1][C:2]([CH2:8][CH2:9][CH3:10])=[C:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH3:11][Li]>C1COCC1.CCOCC.O>[CH3:1][C:2]([C:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1)([CH3:11])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 2

HCID 129395315-(Pentan-2-ylidene)cyclopenta-1,3-dieneHCID 178418348HCID 178418348, compound

Product 1

HCID 12779343HCID 12779343, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.00 g (52.2 mmol) of 6-methyl-6-propylfulvene in 40 ml of THF, 50.3 ml (57.3 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 subjected to vacuum distillation (75° C./5-7 mmHg) to obtain 6.40 g (42.6 mmol) of a light yellow liquid (yield: 82%). 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 and filtered.° From the filtrate
  4. customthe solvent was removed under reduced pressure
  5. customto obtain a liquid
  6. distillationThe liquid was subjected to vacuum distillation (75° C./5-7 mmHg)

Sources & evidence

ORD record
ord-dc71ffc685f2477f81fa7fb60bda6cad
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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