HCID 86726596, compound → HCID 86726593, compound

HRID 589224Notes

Reaction equation

HRID 589224 reaction equation
[CH2:1]([Si:4]([CH2:29][CH:30]=[CH2:31])([CH2:26][CH:27]=[CH2:28])[CH2:5][CH2:6][CH2:7][Si:8]([CH2:13][CH2:14][CH2:15][Si:16]([CH2:23][CH:24]=[CH2:25])([CH2:20][CH:21]=[CH2:22])[CH2:17][CH:18]=[CH2:19])([O:11][CH3:12])OC)[CH:2]=[CH2:3].[C:32]([Li])([CH3:35])([CH3:34])[CH3:33]>CCCCC>[CH2:1]([Si:4]([CH2:29][CH:30]=[CH2:31])([CH2:26][CH:27]=[CH2:28])[CH2:5][CH2:6][CH2:7][Si:8]([CH2:13][CH2:14][CH2:15][Si:16]([CH2:17][CH:18]=[CH2:19])([CH2:20][CH:21]=[CH2:22])[CH2:23][CH:24]=[CH2:25])([C:32]([CH3:35])([CH3:34])[CH3:33])[O:11][CH3:12])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 86726596HCID 86726596, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86726593HCID 86726593, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, bis{3-(triallylsilyl)propyl}dimethoxysilane (29′) (1.0 g, 2.097 mmol) was cooled down to −78° C., then n-pentane solution of 1.61M t-butyllithium 1.954 mL (3.145 mmol) was added dropwise, then stirred at −78° C. for 17 hours. The reacted mixture was cooled down to 0° C., quenched with water, saturated ammonium chloride aqueous solution was added. The obtained organic layer was separated. The obtained water layer was extracted with diethyl ether and the collected organic layer was each washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, obtaining a crude product. The crude product was purified through short silica gel column chromatography (eluent: hexane/ethyl acetate=20/1), obtaining bis({3-(triallylsilyl)propyl}(tert-butyl)methoxysilane (30) (yield: 0.902 g, yield (%): 85%).

Workup

  1. temperatureThe reacted mixture was cooled down to 0° C.
  2. customquenched with water, saturated ammonium chloride aqueous solution
  3. additionwas added
  4. customThe obtained organic layer was separated
  5. extractionThe obtained water layer was extracted with diethyl ether
  6. washeach washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customobtaining a crude product
  11. customThe crude product was purified through short silica gel column chromatography (eluent: hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-e728f2e4e6b54abdaef300b6321eda05
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

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