Trimethylsilyl ether (TMS)

Trimethylsilyl ether (TMS) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • Pyr TMSCl
    CH2Cl2
    0 °C
    15 min
    96 %
    info
    intermediate structure
    Pyr, TMSCl
    CH2Cl2
    0 °C, 15 min, 96%
    intermediate structure
  • Et3N TMSOTf
    CH2Cl2
    -10 to -5 °C
    60 min
    72 %
    info
    intermediate structure
    Et3N, TMSOTf
    CH2Cl2
    -10 to -5 °C, 60 min, 72%
    intermediate structure
  • 2,6-Lutidine TMSOTf
    CH2Cl2
    RT
    4 h
    100 %
    info
    intermediate structure
    2,6-Lutidine, TMSOTf
    CH2Cl2
    RT, 4 h, 100%
    intermediate structure
  • TMSCN
    CH2Cl2
    RT
    15 h
    82 %
    info
    intermediate structure
    TMSCN
    CH2Cl2
    RT, 15 h, 82%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCl
    H2O THF
    0 °C - RT
    60 min - 6 h
    89-100 %
    info
    intermediate structure
    HCl
    H2O, THF
    RT, 60 min, 89%
    intermediate structure
    info
    intermediate structure
    HCl
    THF
    0 °C, 6 h, 100%
    intermediate structure