Ammonium Chloride → HCID 21697900, compound

HRID 379341Notes

Reaction equation

HRID 379341 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH:11]([CH3:13])[CH3:12])[CH:7]=[CH:6][C:5]=2[CH3:14].C([Li])CCC.[Cl-].[CH3:21][SiH:22]([CH3:36])[CH:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2.[Cl-].[NH4+]>CCOCC.CCCCCC>[CH3:21][Si:22]([CH3:36])([CH:3]1[C:4]2[C:9](=[C:8]([CH:11]([CH3:12])[CH3:13])[CH:7]=[CH:6][C:5]=2[CH3:14])[CH:10]=[C:2]1[CH3:1])[CH:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 17776650HCID 17776650, compoundHCID 178418339ButyllithiumHCID 178504336HCID 178504336, compound

Product 1

HCID 21697900HCID 21697900, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 100 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, 2-methyl-4-i-propyl-7-methylindene (1.50 g, 8.06 mmol) and dehydrated ether (25 ml) were introduced. Under stirring at −78° C., a hexane solution of n-butyllithium (8.46 mmol) was dropwise added. After the dropwise addition, the temperature of the system was allowed to spontaneously and slowly rise to room temperature. The reaction mixture was stirred at room temperature over night, whereby a colourless solution came, through a white slurry and a light yellow slurry, to a yellow slurry. To the slurry, the dimethyl(9-fluorenyl)silane chloride (2.06 g, 8.06 mmol) synthesized above was added under stirring at 0° C., followed by stirring at room temperature for 1.5 hours. After ether (100 ml) and a saturated ammonium chloride aqueous solution (100 ml) were added, the resulting mixture was introduced into a separatory funnel to separate out an organic phase. The organic phase was washed with a saturated ammonium chloride aqueous solution, water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the solvent was removed, the obtained product (a yellow oil) was purified by column chromatography (developer: hexane) to obtain 1.50 g so a yellow oil (yield: 46%).

Workup

  1. customA 100 ml four-necked flask equipped with a reflux tube
  2. customa thermometer and a dropping funnel was thoroughly purged with nitrogen
  3. customdried
  4. additionAfter the dropwise addition
  5. customslowly rise to room temperature
  6. stirringThe reaction mixture was stirred at room temperature over night
  7. additionabove was added
  8. stirringunder stirring at 0° C.
  9. stirringby stirring at room temperature for 1.5 hours
  10. additionthe resulting mixture was introduced into a separatory funnel
  11. customto separate out an organic phase
  12. washThe organic phase was washed with a saturated ammonium chloride aqueous solution, water
  13. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  14. customAfter the solvent was removed
  15. customthe obtained product (a yellow oil) was purified by column chromatography (developer: hexane)

Sources & evidence

ORD record
ord-553471ad79d54c32923ad31f47cba513
Source dataset
uspto-grants-2001_10
Patent number
US06297333B1

Reaction notes

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