HCID 15564742, compound → HCID 123152499, compound

HRID 2109645Notes

Reaction equation

HRID 2109645 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]12([Si:17](Cl)(Cl)Cl)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2>CCOCC>[C:7]12([SiH3:17])[CH2:14][CH:13]3[CH2:12][CH:11]([CH2:10][CH:9]([CH2:15]3)[CH2:8]1)[CH2:16]2

Participants

4

Reactant 2

HCID 15564742HCID 15564742, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 123152499HCID 123152499, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (6.18 g) and dry ether (80 mL) were placed in a rb flask. Adamantyl trichlorosilane (50.8 g), dissolved in ether (50 mL) was added dropwise in the magnetically stirred flask at rt. The reaction was allowed to reflux for 24 h. The solution was filtered, evaporated, and 1 mL Et3N in 30 mL pentane was then added and the upper layer was carefully decanted. After evaporation, the crude reaction product was distilled, giving 22 g of adamantylsilane (70%, bp. 40 . . . 50° C./2 mbar). 1H NMR: 1.95 (15H), 3.68 (3H). 13C NMR: 20.63, 28.86, 37.99, 40.61. 29Si NMR: −43.55 (q, Si—H: 190 Hz). Purity was found to be 95.7% by GC.

Workup

  1. additionwas added dropwise in the magnetically stirred flask at rt
  2. temperatureto reflux for 24 h
  3. filtrationThe solution was filtered
  4. customevaporated
  5. addition1 mL Et3N in 30 mL pentane was then added
  6. customthe upper layer was carefully decanted
  7. customAfter evaporation
  8. customthe crude reaction product
  9. distillationwas distilled

Sources & evidence

ORD record
ord-a5ea306af3144fba9ddf06acdb8c2688
Source dataset
uspto-grants-2009_04
Patent number
US07514709B2

Reaction notes

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