Chlorotrimethylsilane → HCID 15319840, compound

HRID 1739646Notes

Reaction equation

HRID 1739646 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:2]1.C1COCC1.[Li]CCCC.[Si:32](Cl)([CH3:35])([CH3:34])[CH3:33]>CCCCCC.O>[CH3:33][Si:32]([CH3:35])([CH3:34])[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:1]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:2]=2)([CH3:12])[CH3:11])=[CH:14]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 109126573,3′-(1-Methylethylidene)bis[1H-indene]HCID 178418339Butyllithium

Product 1

HCID 15319840HCID 15319840, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

3.3 g of 2,2-bis(3-indenyl)propane (20511/46, MW 272.39, 12.11 mmol) and 50 m of THF in a 100 mL flask were cooled to -70° C. while stirring. 17 mL of a 1.6 M solution of BuLi (27.2 mmol) in hexane were added dropwise. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The solution was cooled again to -70° C. and 3.4 mL of Me3SiCl (MW 108.64, d 0.856, 26.8 mmol) were added. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 h. Water is then added, the organic layer is separated and the water layer extracted twice with Et2O, all organic phases were combined and dried over MgSO4, then filtered and all volatiles removed in vacuo. 4.8 g (95%) of a mixture of rac/meso 2,2-bis(1-trimethylsilyl-3-indenyl)propane was obtained. 1H NMR (200 MHz, C2D2Cl4, 120° C., referenced to the peak of residual C2HDCl4 at 5.75 ppm): 7.1-7.3 (m, 4H, C6 ring), 6.75-6.95 (m, 4H, C6 ring), 6.3-6.4 (br s, 2H, C5 ring), 3.2-3.3 (m, 2H, C5 ring), 1.64, 1.62 (2 s, 6H, bridge methyls), -0.15, -0.17 (2 s, 18H, TMS methyls).

Workup

  1. additionAt the end of the addition
  2. stirringstirred for 1 h
  3. temperatureThe solution was cooled again to -70° C.
  4. additionAt the end of the addition
  5. temperatureto warm to room temperature
  6. stirringstirred for 2 h
  7. customthe organic layer is separated
  8. extractionthe water layer extracted twice with Et2O
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customall volatiles removed in vacuo

Sources & evidence

ORD record
ord-ab133960c4b34d1298b4af1518bb3088
Source dataset
uspto-grants-1999_10
Patent number
US05968863

Reaction notes

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