[2-(Trimethylsilyl)ethoxy]methyl acetal (SEM)

[2-(Trimethylsilyl)ethoxy]methyl acetal (SEM) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TMS(CH2)2OCH2Cl KH 18-Crown-6
    THF
    RT
    5 h
    84 %
    intermediate structure
    KH, 18-Crown-6, TMS(CH2)2OCH2Cl
    THF
    RT, 5 h, 84%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • n-Bu4N+ F-
    HMPA
    50 °C
    12 h
    60 %
    intermediate structure
    n-Bu4N+ F-
    HMPA
    50 °C, 12 h, 60%
    intermediate structure