Indene → Lithium, 1H-inden-1-yl-

HRID 1069787Notes

Reaction equation

HRID 1069787 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Li:14])CCC>>[CH-:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+:14]

Participants

3

Reactant 2

HCID 7219IndeneHCID 178418339Butyllithium4×

Product 1

HCID 11116044Lithium, 1H-inden-1-yl-Yield 99%

Conditions

Temperature
38 °C

Procedure

Under N2 a mixture of 51.6 g (0.115 mole) of technical grade indene (92.5% by GC analysis, pre-purified by a neutral alumina column), 186.3 g of dry diethyl ether and 8.0 g of dried (over 4 Å molecular sieve) toluene was placed in a 1-L flask. The flask was equipped with an agitator, a condenser and thermometer. To the mixture a total of 172 mL (0.4316 mole) of n-butyllithium (2.5 M in hexanes) was added dropwise in 2 portions. The pot temperature was allowed to raise to reflux (38° C.) during the addition. When 150 mL of butyllithium were added, the addition was stopped and the analysis (NMR) of the mixture indicated that 22 mL more of butyllithium were needed to finish the reaction. After feeding the calculated amount of butyllithium, the final analysis of the reaction mixture showed 99% conversion and 99% yield of lithium-indenide (Li-Ind). The mixture was used as such for the next reaction.

Workup

  1. custompre-purified by a neutral alumina column), 186.3 g of dry diethyl ether and 8.0 g
  2. dry with materialof dried (over 4 Å molecular sieve) toluene
  3. customwas placed in a 1-L flask
  4. customThe flask was equipped with an agitator, a condenser and thermometer
  5. temperatureto raise
  6. additionduring the addition
  7. additionthe addition
  8. customthe reaction

Sources & evidence

ORD record
ord-f269518f05b348c382413359a52baabe
Source dataset
uspto-grants-2001_06
Patent number
US06252098B1

Reaction notes

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