Chlorotrimethylsilane → 2-{2-[1-(trimethylsilyl)-1H-inden-3-yl]ethyl}pyridine

HRID 1983808Notes

Reaction equation

HRID 1983808 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:2]1.C([Li])CCC.CCCCCC.[Si:29](Cl)([CH3:32])([CH3:31])[CH3:30].[Cl-].[NH4+]>C(OCC)C.O>[CH3:30][Si:29]([CH3:32])([CH3:31])[CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:2]1

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 121355622-[2-(1H-inden-3-yl)ethyl]pyridineHCID 178418339Butyllithium

Product 1

HCID 179629802-{2-[1-(trimethylsilyl)-1H-inden-3-yl]ethyl}pyridineYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-90 °C

Procedure

2-[2-(1H-inden-3-yl)ethyl]pyridine (14.88 g, 0.0637 mol) was dissolved in 190 ml of diethylether. The resulting solution was cooled to −90° C. and then 15% n-butyllithium in hexane (42.08 ml, 67.3 mmol) added. The resulting mixture was stirred at this temperature for an additional 30 min and then allowed to reach room temperature. After additional stirring for 1 h at room temperature, the mixture was cooled to −90° C. and was then treated with a solution of SiMe3Cl (9.4 ml, 74 mmol) in 10 ml of diethylether. The resulting mixture was allowed to warm to room temperature and then stirred for 12 h. Then the mixture was first treated with water and then aqueous ammonium chloride solution. The organic phase was separated and the aqueous phase extracted three times with diethylether. The combined organic phase was washed with brine and dried over MgSO4. After filtration, the solvent was removed from the filtrate to give 15.97 g (81%) of 2-{2-[1-(trimethylsilyl)-1H-inden-3-yl]ethyl}pyridine as an oil, which was used in the next stage without separation.

Workup

  1. customto reach room temperature
  2. stirringAfter additional stirring for 1 h at room temperature
  3. temperaturethe mixture was cooled to −90° C.
  4. temperatureto warm to room temperature
  5. stirringstirred for 12 h
  6. customThe organic phase was separated
  7. extractionthe aqueous phase extracted three times with diethylether
  8. washThe combined organic phase was washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationAfter filtration
  11. customthe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-e0d90ee718204b5f807c6d9b025f5c37
Source dataset
uspto-grants-2009_06
Patent number
US07541481B2

Reaction notes

Loading…