Methoxymethyl acetal (MOM)

Methoxymethyl acetal (MOM) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • MeOCH2Cl i-Pr2NEt
    CH2Cl2
    RT - 50 °C
    4 - 18 h
    90-98 %
    intermediate structure
    MeOCH2Cl, i-Pr2NEt
    CH2Cl2
    50 °C, 4 h, 90%
    intermediate structure
    intermediate structure
    MeOCH2Cl, i-Pr2NEt
    CH2Cl2
    RT, 18 h, 98%
    intermediate structure
    intermediate structure
    MeOCH2Cl, i-Pr2NEt
    CH2Cl2
    RT, 18 h, 98%
    intermediate structure
  • CH2(OMe)2 P2O5
    CHCl3
    RT
    4 h
    86 %
    intermediate structure
    CH2(OMe)2, P2O5
    CHCl3
    RT, 4 h, 86%
    intermediate structure
  • MeOCH2Cl i-Pr2NEt DMAP
    CH2Cl2
    0 °C - RT
    16 h
    71-97 %
    intermediate structure
    MeOCH2Cl, i-Pr2NEt, DMAP
    CH2Cl2
    0 °C to RT, 16 h, 97%
    intermediate structure
    intermediate structure
    MeOCH2Cl, i-Pr2NEt, DMAP
    CH2Cl2
    0 °C to RT, 16 h, 96%
    intermediate structure
    intermediate structure
    MeOCH2Cl, i-Pr2NEt, DMAP
    CH2Cl2
    0 °C to RT, 16 h, 71%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCl
    MeOH H2O
    RT
    3 - 8 h
    89-93 %
    intermediate structure
    HCl
    MeOH, H2O
    RT, 8 h, 93%
    intermediate structure
    intermediate structure
    HCl
    MeOH, H2O
    RT, 3 h, 89%
    intermediate structure
  • HBr
    MeCN H2O
    RT
    2 h
    95 %
    intermediate structure
    HBr
    MeCN, H2O
    RT, 2 h, 95%
    intermediate structure
  • TMSBr
    CH2Cl2
    0 °C
    30 min
    100 %
    intermediate structure
    TMSBr
    CH2Cl2
    0 °C, 30 min, 100%
    intermediate structure