Benzyloxymethyl acetal (BOM)

Benzyloxymethyl acetal (BOM) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • BnOCH2Cl i-Pr2NEt n-Bu4N+ I-
    CH2Cl2
    Reflux
    32 h
    92 %
    info
    intermediate structure
    BnOCH2Cl, i-Pr2NEt, n-Bu4N+ I-
    CH2Cl2
    Reflux, 32 h, 92%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • H2 Pd/C
    EtOH
    Reflux
    45 min
    94 %
    info
    intermediate structure
    H2, Pd/C
    EtOH
    Reflux, 45 min, 94%
    intermediate structure
  • HCl NaI
    Acetone H2O
    RT
    21 h
    65 %
    info
    intermediate structure
    HCl, NaI
    Acetone, H2O
    RT, 21 h, 65%
    "97 % yield based on 67 % conversion."
    intermediate structure