Hydrochloric Acid → HCID 131729266, compound

HRID 556126Notes

Reaction equation

HRID 556126 reaction equation
[CH2:1]([O:3][Si:4](OCC)(OCC)[C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:28]2[CH:33]=[CH:32][C:31]([Si:34](OCC)(OCC)[O:35][CH2:36][CH3:37])=[CH:30][CH:29]=2)[C:12]2[CH:17]=[CH:16][C:15]([Si:18](OCC)(OCC)[O:19][CH2:20][CH3:21])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH2:50]([Mg]Br)[CH:51]=[CH2:52].Cl>CCOCC>[CH2:50]([CH:37]([CH2:16][CH:15]=[CH2:14])[CH2:36][O:35][SiH2:34][C:31]1[CH:32]=[CH:33][C:28]([N:11]([C:12]2[CH:13]=[CH:14][C:15]([SiH2:18][O:19][CH2:20][CH:21]([CH2:10][CH:5]=[CH2:6])[CH2:17][CH:12]=[CH2:13])=[CH:16][CH:17]=2)[C:8]2[CH:9]=[CH:10][C:5]([SiH2:4][O:3][CH2:1][CH:2]([CH2:33][CH:28]=[CH2:29])[CH2:9][CH:8]=[CH2:7])=[CH:6][CH:7]=2)=[CH:29][CH:30]=1)[CH:51]=[CH2:52]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 57587318HCID 57587318, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 131729266HCID 131729266, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Firstly, dist. ether (5 mL) was added to tris(4-triethoxysilylphenyl)amine (242 mg, 0.33 mmol) under a nitrogen atmosphere. Then, 1-M allylmagnesium bromide (4 mL (solvent: ether), 4 mmoL) was added dropwise at 0° C. The resultant mixture was stirred under a nitrogen atmosphere at room temperature for 20 hours to obtain a mixture. Subsequently, the mixture was added with an aqueous solution of HCl of 10% by mass to cease the reaction, and the pH of an aqueous layer was adjusted to 4 by using an aqueous solution of HCl of 10% by mass. After that, an organic layer was separated, and the aqueous layer was extracted with ether. The organic layer thus collected was washed with sat. NaHCO3 and sat. NaCl, and was dried with MgSO4. The dried organic layer was then filtered and concentrated to obtain a crude product. Subsequently, the crude product was separated and purified by PTLC (hexane/EtOAc=10/1) to obtain tris(4-diallylethoxysilylphenyl)amine (80 mg, 34% yield).

Workup

  1. customto obtain a mixture
  2. customthe reaction
  3. customAfter that, an organic layer was separated
  4. extractionthe aqueous layer was extracted with ether
  5. customThe organic layer thus collected
  6. washwas washed with sat. NaHCO3 and sat. NaCl
  7. dry with materialwas dried with MgSO4
  8. filtrationThe dried organic layer was then filtered
  9. concentrationconcentrated
  10. customto obtain a crude product
  11. customSubsequently, the crude product was separated
  12. custompurified by PTLC (hexane/EtOAc=10/1)

Sources & evidence

ORD record
ord-0be836b9155d466f8a42f94d743a4bbb
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

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