Chlorotrimethylsilane → 3-((trimethylsilyl)oxy)indene

HRID 1953946Notes

Reaction equation

HRID 1953946 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1(=[O:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.[CH3:23][Si:24](Cl)([CH3:26])[CH3:25]>O1CCCC1.CCCCCC>[CH3:23][Si:24]([CH3:26])([CH3:25])[O:22][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 67351-IndanoneHCID 7912DiisopropylamineHCID 178418339Butyllithium

Product 1

HCID 110635583-((trimethylsilyl)oxy)indene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 2-liter flask were charged 38.2 g (0.378 mol) of diisopropylamine and 265 ml of tetrahydrofuran (THF). The mixture was cooled to 0° C. and 229 ml of a hexane solution of 1.65 M n-butyllithium was added thereto. After 15 minutes' stirring, the mixture turned dark brown. The solution was further cooled to -78° C., to which was added 50 ml of a THF solution of 50 g (378 mmol) of 1-indanone and the resulting mixture was stirred for 30 minutes. Then, 205 g (1.89 mol) of trimethylsilyl chloride was added at -78° C., and the coolant was removed to raise the temperature to room temperature followed by stirring for 2 hours.

Workup

  1. temperatureThe solution was further cooled to -78° C., to which
  2. stirringthe resulting mixture was stirred for 30 minutes
  3. customthe coolant was removed
  4. temperatureto raise the temperature to room temperature
  5. stirringby stirring for 2 hours

Sources & evidence

ORD record
ord-aafbc6b657224d8d9756eebfcdf0a387
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

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