Chlorotrimethylsilane → HCID 87437838, compound

HRID 1877722Notes

Reaction equation

HRID 1877722 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[Li]CCCC.Cl[Si:14]([CH3:17])([CH3:16])[CH3:15].[Cl-].[Li+]>O1CCCC1>[N:5]([CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])([Si:14]([CH3:17])([CH3:16])[CH3:15])[Si:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6397Chlorotrimethylsilane2×HCID 89728Aminoacetaldehyde dimethyl acetalHCID 433294Lithium Chloride2×HCID 178418339Butyllithium2×

Product 1

HCID 87437838HCID 87437838, compoundYield 128.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, 5.25 g (0.05 moles) of aminoacetaldehyde dimethylacetal were dissolved in 50 ml of dry tetrahydrofuran and cooled to −78° C. 20 ml of 2.5M nBuLi (0.05 moles) were then added over 5 minutes with stirring. The mixture was then stirred for 15 minutes at −78 C then allowed to slowly warm to room temperature. 6.3 ml (0.05 moles) of chlorotrimethylsilane were then added over 20 minutes and the reaction allowed to stir for an additional 30 minutes. During this addition the mixture increased in temperature and a precipitate of lithium chloride was observed to form. The mixture was then cooled back down to −78 C and an additional 20 ml of 2.5M nBuLi added over 5 minutes with stirring and the mixture was held at this temperature for an additional 15 minutes before being allowed to warm back up to room temperature. An additional 6.3 ml of chlorotrimethylsilane was then added over a 20 minute period with stirring, during which time the mixture was observed to warm up and additional lithium chloride form. The Mixture was then stirred for an additional 30 minutes before being filtered. The tetrahydrofuran was then removed from the filtrate by vacuum and the final product was vacuum distilled from the remaining filtrate. This resulted in a yield of 8.0 g (64% of theoretical) of (Me3Si)2NCH2CH(OMe)2.

Workup

  1. stirringThe mixture was then stirred for 15 minutes at −78 C
  2. temperatureto slowly warm to room temperature
  3. stirringto stir for an additional 30 minutes
  4. additionDuring this addition the mixture
  5. temperatureincreased in temperature
  6. customto form
  7. temperatureThe mixture was then cooled back down to −78 C
  8. stirringwith stirring
  9. temperatureto warm back up to room temperature
  10. stirringwith stirring, during which time the mixture
  11. temperatureto warm up
  12. stirringThe Mixture was then stirred for an additional 30 minutes
  13. filtrationbefore being filtered
  14. customThe tetrahydrofuran was then removed from the filtrate by vacuum
  15. distillationdistilled from the remaining filtrate

Sources & evidence

ORD record
ord-e004a5f3e2574b518d41d0da17023689
Source dataset
uspto-grants-2012_11
Patent number
US08313807B2

Reaction notes

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