Tetraethoxysilane → HCID 58560611, compound

HRID 571450Notes

Reaction equation

HRID 571450 reaction equation
[Si:1]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[Mg]Br.CCCCC>C1COCC1>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[Si:1]([O:5][CH2:6][CH3:7])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6517TetraethoxysilaneHCID 8003PentaneHCID 178425415HCID 178425415, compound

Product 1

HCID 58560611HCID 58560611, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To tetraethyl orthosilicate (3.30 mL, 15.0 mmol, 3.00 equiv) in 10 mL of THF at −30° C. was added 2,4,6-trimethylphenylmagnesium bromide solution (1.0 M in THF, 5.0 mL, 5.0 mmol, 1.0 equiv) dropwise over 10 min. After stiffing at −30° C. for 1 h, the reaction mixture was warmed to 23° C. and was further stirred for 12 h. The reaction mixture was poured into 100 mL of pentane, and was washed three times with water (3×20 mL) and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure. Bulb-to-bulb distillation (125° C., 0.5 Torr) afforded 0.87 g of the title compound as a colorless oil (62% yield). Rf=0.14 (hexanes). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23° C., δ): 6.80 (s, 2H), 3.83 (q, J=7.0 Hz, 6H), 2.51 (s, 6H), 2.26 (s, 3H), 1.24 (t, J=7.0 Hz, 9H). 13C NMR (125 MHz, CDCl3, 23° C., δ): 145.92, 139.79, 128.81, 124.99, 58.10, 23.73, 21.08, 18.15.

Workup

  1. washwas washed three times with water (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration
  4. customthe solvent was removed under reduced pressure
  5. distillationdistillation (125° C., 0.5 Torr)

Sources & evidence

ORD record
ord-fb18e8e8b6eb422b959a04497b69f55a
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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