HCID 85774823, compound → HCID 118413259, compound

HRID 1485807Notes

Reaction equation

HRID 1485807 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[CH2:5][C:6]=1C.[Li]CCCC>CCOCC>[CH3:13][C:10]1[O:9][C:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH2:6][CH:5]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 85774823HCID 85774823, compoundHCID 178418339Butyllithium

Product 1

HCID 118413259HCID 118413259, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The solution of 2-(3,4-dimethyl-1,3-cyclopentadien-1-yl)-5-methylfuran (3.2 g, 20 mmol) in Et2O (40 mL) was cooled to −20° C. and BuLi (8 mL 2.5N in hexane, 20 mmol) was added dropwise. Suspension obtained was stirred 1 h at room temperature, cooled again to −20° C., and ZrCl4(THF)2 (3.77 g, 10 mmol) was added. After 16 h of stirring, the precipitate was filtered off, dissolved in dichloromethane, solution was filtered and solvent was evaporated. Residue was washed with Et2O, pentane and dried in vacuo giving 0.6 g of product as pure form. Filtrate was concentrated and 1.3 g of complex was obtained as mixture of isomers (1:1 ratio). (total yield 38%).

Workup

  1. customSuspension obtained
  2. temperaturecooled again to −20° C.
  3. stirringAfter 16 h of stirring
  4. filtrationthe precipitate was filtered off
  5. dissolutiondissolved in dichloromethane
  6. filtrationsolution was filtered
  7. customsolvent was evaporated
  8. washResidue was washed with Et2O, pentane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-72ed209bdef34fdca3b0f3aa36f01bcd
Source dataset
uspto-grants-2016_08
Patent number
US09422319B2

Reaction notes

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