Methyl iodide → HCID 21697905, compound

HRID 612430Notes

Reaction equation

HRID 612430 reaction equation
[CH3:1][Si:2]([CH3:25])([CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)[CH:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[CH2:26]([Li])CCC.CI.[Cl-].[NH4+]>CCOCC.CCCCCC>[CH3:1][Si:2]([CH3:25])([CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH3:26])=[CH:17]1)[CH:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 15793108HCID 15793108, compoundHCID 178418339Butyllithium

Product 1

HCID 21697905HCID 21697905, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A 200 ml four-necked flask equipped with a reflux tube, a thermometer and a dropping funnel was thoroughly purged with nitrogen and dried. To the flask, dimethyl(1-indenyl)(9-fluorenyl)silane (2.00 g, 5.91 mmol) synthesized above and dehydrated ether (50 ml) were introduced. To the flask was dropwise added a hexane solution of n-butyllithium (6.21 mmol) at -40° C. with stirring. The temperature of the reaction liquid was allowed to spontaneously and slowly rise to room temperature. After stirring over night, the reaction liquid became a yellow solution. To the solution, methyl iodide (3.78 g, 26.6 mmol) was added and the temperature of the system was allowed to spontaneously and slowly rise to room temperature, followed by stirring for one day. The reaction liquid became an orange solution. To the resulting solution, 100 ml of ether and 100 ml of a saturated aqueous solution of ammonium chloride were added and the mixture was introduced into a separatory funnel to separate an organic phase. The organic phase was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off, it was purified by column chromatography (developer: hexane) to obtain two kinds of isomers (one was a colourless transparent liquid, the other was a yellow liquid) totalling to 1.85 g (yield: 89%).

Workup

  1. customA 200 ml four-necked flask equipped with a reflux tube
  2. customa thermometer and a dropping funnel was thoroughly purged with nitrogen
  3. customdried
  4. additionwere introduced
  5. customThe temperature of the reaction liquid
  6. customslowly rise to room temperature
  7. stirringAfter stirring over night
  8. customthe reaction liquid
  9. customslowly rise to room temperature
  10. stirringby stirring for one day
  11. customThe reaction liquid
  12. additionthe mixture was introduced into a separatory funnel
  13. customto separate an organic phase
  14. washThe organic phase was washed with water
  15. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  16. distillationAfter the solvent was distilled off
  17. customit was purified by column chromatography (developer: hexane)
  18. customto obtain two kinds of isomers (one

Sources & evidence

ORD record
ord-e5f5327b05dd45b785374ce974b78914
Source dataset
uspto-grants-1999_12
Patent number
US06004897

Reaction notes

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