BIS(TRIETHOXYSILYL)METHANE → HCID 178506912, compound

HRID 1061478Notes

Reaction equation

HRID 1061478 reaction equation
[CH2:1]([O:3][Si:4]([CH2:11][Si:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2].C([Li:26])(C)(C)C>>[CH2:17]([O:16][Si:12]([CH:11]([Li:26])[Si:4]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])([O:19][CH2:20][CH3:21])[O:13][CH2:14][CH3:15])[CH3:18]

Participants

3

Reactant 2

HCID 9798044BIS(TRIETHOXYSILYL)METHANE2×HCID 178418306HCID 178418306, compound

Product 1

HCID 178506912HCID 178506912, compound

Conditions

Temperature
-78 °C

Procedure

A commercially available bis(triethoxysilyl)methane (BTM) was lithiated by the following procedure. To 300 mL of freshly distilled dry tetrahydrofuran (THF) in a 3-neck flask attached to a bubbler was added 3.07 g (9.00 mmol) BTM and the solution was flushed for 5 minutes with nitrogen that had been passed through a drying column packed with CaCl2 and Drierite. The solution was cooled down to −78° C. and then 5.2 mL, 1.7 M (9 mmol) of t-butyllithium was added dropwise over 10 minutes. The solution was stirred for 30 minutes at −78° C. after which a very, faint yellowish solution resulted. Then the temperature of the solution was raised to room temperature (RT) and stirring continued for 30 minutes at RT after which the solution turned colorless.

Workup

  1. distillationTo 300 mL of freshly distilled dry tetrahydrofuran (THF) in a 3-neck flask
  2. customthe solution was flushed for 5 minutes with nitrogen that
  3. customresulted
  4. temperatureThen the temperature of the solution was raised to room temperature (RT)
  5. stirringstirring
  6. waitcontinued for 30 minutes at RT

Sources & evidence

ORD record
ord-56ec9beedeac474d9ecb0826c96b1080
Source dataset
uspto-grants-2005_11
Patent number
US06960551B2

Reaction notes

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