Indene → HCID 15849142, compound

HRID 585167Notes

Reaction equation

HRID 585167 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O1CCCC1.C([Li])CCC.[CH2:20]1[CH2:30][CH2:29][C:23](=[C:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)[CH2:22][CH2:21]1>O>[CH:24]1([C:23]2([CH:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)[CH2:29][CH2:30][CH2:20][CH2:21][CH2:22]2)[CH:25]=[CH:26][CH:27]=[CH:28]1

Participants

6

Reactant 4

HCID 7219IndeneHCID 8028TetrahydrofuranHCID 575532HCID 575532, compoundHCID 178418339Butyllithium

Product 1

HCID 15849142HCID 15849142, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Indene (5.8 g, 50 mmole) was placed in a 250 ml round bottom flask with 50 ml of THF (tetrahydrofuran). 34.3 ml (1.6 M, 55 mmole) of n-butyl lithium (n-BuLi) was added into the solution under an ice bath. The mixture turned orange red. The ice bath was removed and the mixture was stirred for 3 hours. 6.7 g of 6,6-pentamethylenefulvene (46 mmole) was added gradually to the mixture. After stirring for 24 hours, 1 ml of water was added to the mixture to terminate the reaction. The reaction mixture was stripped under vacuum to remove solvent, washed with 100 ml of pentane, and filtered to remove the salt. The crude product (i.e., filtrate) was purified by column chromatography (the packing was 20 g of silica gel, the eluent was 100% pentane). The solution was then concentrated under reduced pressure to obtain a pale yellow liquid (8.3 g, yield=69%).

Workup

  1. customThe ice bath was removed
  2. stirringAfter stirring for 24 hours
  3. customto terminate
  4. customthe reaction
  5. customto remove solvent
  6. washwashed with 100 ml of pentane
  7. filtrationfiltered
  8. customto remove the salt
  9. customThe crude product (i.e., filtrate) was purified by column chromatography (the packing
  10. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a505f091da84c3b941f2d1e607a25e4
Source dataset
uspto-grants-2005_08
Patent number
US06930157B2

Reaction notes

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