Chlorotrimethylsilane → HCID 21709893, compound

HRID 650886Notes

Reaction equation

HRID 650886 reaction equation
[O:1]([C:9]1[CH:10]([CH:18]([CH:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[C:21]2[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH3:19])[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Li]CCCC.Cl[Si:43]([CH3:46])([CH3:45])[CH3:44]>C1COCC1.CCCCCC>[CH3:44][Si:43]([CH3:46])([CH3:45])[CH:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]([Si:2]([CH3:5])([CH3:4])[CH3:3])[C:21]=2[O:29][Si:30]([C:33]([CH3:35])([CH3:34])[CH3:36])([CH3:31])[CH3:32])[CH3:19])=[C:9]1[O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 21709885HCID 21709885, compoundHCID 178418339Butyllithium

Product 1

HCID 21709893HCID 21709893, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of bis(2-(tert-butyldimethylsiloxy)indenyl)ethane (10.38 g, 20.0 mmol) in THF (100 mL) at −20° C. was added dropwise n-BuLi (16.1 mL of a 2.5 M solution in hexane, 40.2 mmol) and the reaction mixture was stirred for 3 hours at room temperature. To the resulting solution was added dropwise chlorotrimethylsilane (6.85 g, 63.0 mmol, 8.0 mL) at 0° C. After completed addition the reaction mixture was stirred overnight at room temperature and the solvents were evaporated. The remaining orange solid was extracted with CH2Cl2 and filtrated through celite. The solvent was evaporated and the product was dissolved in Et2O (150 mL). Concentration and cooling to 0° C. gave 10.29 g (77.6%) of a 2:1 diastereomeric mixture of the title compound as off-white crystals. EIMS (calcd/found): m/e 662.3827/662.3834. 1H NMR (CD2Cl2, δ, major/minor diastereomer): 7.51-7.49 (m, 2H, major); 7.42-7.40 (m, 2H, minor); 7.29-7.24 (m, 4+2H, major/minor); 7.22-7.17 (m, 2H, minor); 7.08-7.02 (m, 2+2H, major/minor); 3.29 (s, 1H, minor); 3.27 (s, 1H, major); 3.00-2.96 (m, AA′, 2H, minor); 2.72-2.65 (m, AA′BB′, 4H, major); 2.44-2.40 (m, BB′, 2H, minor); 1.02 (s, 18H, major); 1.01 (s, 18H, minor); 0.20 (s, 6H, minor); 0.19 (s, 6H, major); 0.10 (s, 6H, minor); 0.05 (s, 6H, major); 0.02 (s, 18H, minor); 0.01 (s, 18H, major). 13C NMR (CD2Cl2, δ, major diastereomer): 158.32; 144.56; 139.24; 125.09; 122.74; 121.98; 119.89; 118.08; 45.08; 26.14; 24.06; 18.52; −2.39; −3.40; −4.66. 13C NMR (CDCl3, δ, minor diastereomer): 158.08; 144.50; 139.14; 124.97; 122.62; 121.95; 119.95; 118.50; 45.13; 26.14; 23.86; 18.47; −2.29; −3.40; −4.24.

Workup

  1. additionaddition the reaction mixture
  2. stirringwas stirred overnight at room temperature
  3. customthe solvents were evaporated
  4. extractionThe remaining orange solid was extracted with CH2Cl2
  5. filtrationfiltrated through celite
  6. customThe solvent was evaporated
  7. dissolutionthe product was dissolved in Et2O (150 mL)
  8. concentrationConcentration
  9. temperaturecooling to 0° C.
  10. customgave

Sources & evidence

ORD record
ord-435498d41dc34c1ba61e264c5b754adc
Source dataset
uspto-grants-2001_08
Patent number
US06277778B1

Reaction notes

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