Ammonium Chloride → HCID 21697914, compound

HRID 612434Notes

Reaction equation

HRID 612434 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:11].[CH2:12]([Li])[CH2:13]CC.[Cl-].[CH3:18][SiH:19]([CH3:33])[CH:20]1[C:32]2[CH:31]=CC=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2.[Cl-].[NH4+]>CCCCCC.CCOCC>[CH3:33][Si:19]([CH3:18])([CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]([CH3:28])=[C:32]1[CH3:31])[CH:4]1[C:3]2[CH:11]=[CH:13][CH:12]=[CH:1][C:2]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 406381,2-Dimethyl-1H-indeneHCID 178418339ButyllithiumHCID 178504336HCID 178504336, compound

Product 1

HCID 21697914HCID 21697914, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent2×

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, the 1,2-dimethylindene (1.60 g, 11.09 mmol) synthesized above and dehydrated ether (40 ml) were introduced. To the flask, a hexane solution of n-butyllithium (11.6 mmol) was dropwise added at 0° C. with stirring. The temperature of the system was allowed to spontaneously and slowly rise to room temperature. After stirring over night, the reaction liquid became a milk white slurry. To the slurry, the dimethyl(9-fluorenyl)silane chloride (2.72 g, 10.51 mmol) synthesized above was added, followed by stirring at room temperature for 2 hours. The reaction liquid became a yellow slurry. To the slurry, N-methyl-2-pyrrolidine (0.1 g) was added, followed by stirring at room temperature for 1.5 hours. To the resultant mixture, 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 a saturated aqueous solution of ammonium chloride, 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 1.01 g of a yellow powder (yield: 27%).

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. customslowly rise to room temperature
  6. stirringAfter stirring over night
  7. customthe reaction liquid
  8. additionabove was added
  9. stirringby stirring at room temperature for 2 hours
  10. customThe reaction liquid
  11. stirringby stirring at room temperature for 1.5 hours
  12. additionthe mixture was introduced into a separatory funnel
  13. customto separate an organic phase
  14. washThe organic phase was washed with a saturated aqueous solution of ammonium chloride, 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

Sources & evidence

ORD record
ord-1f6a97de8650442691a2530ec3bbad7e
Source dataset
uspto-grants-1999_12
Patent number
US06004897

Reaction notes

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