Methyl iodide → HCID 178420585, compound

HRID 2417639Notes

Reaction equation

HRID 2417639 reaction equation
[CH:1]1[C:14]2[C:5](=C[C:7]3[C:12]([CH:13]=2)=CC=CC=3)C=CC=1.[CH:15]1[CH2:19][CH:18]=[CH:17][CH:16]=1.[Mg].CI.Cl[Ti:24](Cl)(Cl)Cl>C1COCC1>[CH:5]1[C:14](=[CH2:1])[CH:13]=[CH:12][CH:7]=1.[CH:16]1([Ti:24][CH:7]2[CH:12]=[CH:13][CH:14]=[CH:5]2)[CH:15]=[CH:19][CH:18]=[CH:17]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 7612CyclopentadieneHCID 8418AnthraceneHCID 24193Titanium TetrachlorideHCID 5462224Magnesium

Product 1

HCID 178420585HCID 178420585, compoundYield 1,863.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
69 °C

Procedure

Following the procedure of Example 1, 1.1 g (6.2 mMoles) of anthracene and 42.7 g of cyclopentadiene are added to 10.94 g (450 mMoles) of fine magnesium powder in 300 ml of THF, followed by activation with 0.1 ml of methyliodide and by treatment for 3 hours in an ultrasonic bath. 56.9 g (33 ml=300 mMoles) of TiCl4 are then added dropwise, which initiates an extremely vigorous reaction and an increase in temperature to 69° C. After the addition, the mixture is allowed to cool to 23° C. and 14.8 g of a scarlet-red compound are obtained after 12 hours, being isolated by filtration. Another 69.1 g are obtained from the filtrate by concentration. Total yield: 83.9 g of C5H4 --C5H4Ti2 (C5H5)2Cl2 corresponding to 179.9 mMoles=66% of the theoretical.

Workup

  1. customan extremely vigorous reaction
  2. additionAfter the addition
  3. temperatureto cool to 23° C.

Sources & evidence

ORD record
ord-f9a544771e4d437ba344199db74cf76c
Source dataset
uspto-grants-1984_09
Patent number
US04469638

Reaction notes

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