Chlorotrimethylsilane → HCID 54362776, compound

HRID 1735630Notes

Reaction equation

HRID 1735630 reaction equation
C[Si]([N-:5][Si:6]([CH3:9])([CH3:8])[CH3:7])(C)C.[Li+].[CH3:11][Si:12]([CH3:18])([CH3:17])[C:13]#[C:14][CH:15]=O.C[Si](Cl)(C)C>>[CH3:9][Si:6]([CH3:7])([CH3:8])[N:5]=[CH:15][C:14]#[C:13][Si:12]([CH3:18])([CH3:17])[CH3:11]

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 27608653-TRIMETHYLSILYLPROPYNAL2×

Product 1

HCID 54362776HCID 54362776, compound

Procedure

Lithium bis(trimethylsilyl)amide is placed in a reaction vessel to which 3-(trimethylsilyl)-2-propynal of step 1 is added in an aprotic solvent. During the addition of 3-(trimethylsilyl)-2-propynal the pot temperature should be maintained between -40° to -20° C. to ensure stability of the intermediate imine. To the resulting solution is added trimethylsilyl chloride and the resulting mixture stirred at a temperature ranging from -40° to -20° C. for 1 hour. This reaction step yields N,3-bis(trimethylsilyl)-2-propyn-1-imine which is not isolated from the vessel but is confirmed by GC. To the reaction vessel is now added t-butyl acetate and a catalytic amount of lithium bis(trimethylsilyl)amide. The reaction mixture is allowed to stir for 2 h at a temperature ranging from -40° to -20° C. to give (±)1,1-dimethylethyl 3-amino-5-(trimethylsilyl)-4-pentynoate which is isolated after an aqueous ammonium chloride quench and used in the next step. In order to insure complete cleavage of the nitrogen-silicon bond the stir time for this phase should not be less than 30 minutes.

Workup

  1. additionis added in an aprotic solvent
  2. temperatureshould be maintained between -40° to -20° C.
  3. customThis reaction step

Sources & evidence

ORD record
ord-5e6dc4cf286447ecaaa99dddb174bc09
Source dataset
uspto-grants-1996_07
Patent number
US05536869

Reaction notes

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