Methoxymethyl acetal (MOM)

Methoxymethyl acetal (MOM) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • MeOCH2Cl i-Pr2NEt
    CH2Cl2
    0 °C to RT
    3 h - ON
    85-98 %
    intermediate structure
    MeOCH2Cl, i-Pr2NEt
    CH2Cl2
    0 °C to RT, ON, 98%
    intermediate structure
    intermediate structure
    MeOCH2Cl, i-Pr2NEt
    CH2Cl2
    0 °C to RT, 3 h, 85%
    intermediate structure
  • MeOCH2Cl NaH n-Bu4N+ I-
    DMF
    0 °C to RT
    24 - 72 h
    71-91 %
    intermediate structure
    MeOCH2Cl, NaH, n-Bu4N+ I-
    DMF
    0 °C to RT, 24 h, 91%
    intermediate structure
    intermediate structure
    MeOCH2Cl, NaH, n-Bu4N+ I-
    DMF
    RT, 72 h, 71%
    intermediate structure
  • MeOCH2Cl NaH
    DMF
    0 °C - RT
    2 h
    74-96 %
    intermediate structure
    MeOCH2Cl, NaH
    DMF
    0 °C to RT, 2 h, 74%
    intermediate structure
    intermediate structure
    MeOCH2Cl, NaH
    DMF
    0 °C to RT, 2 h, 96%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCl
    MeOH H2O
    -12 °C - RT
    7 h - 3 d
    65-85 %
    intermediate structure
    HCl
    MeOH, H2O
    RT, 3 d, 85%
    intermediate structure
    intermediate structure
    HCl
    MeOH
    -12 to 0 °C, 7 h, 65%
    intermediate structure
  • HBr
    CH2Cl2
    0 °C
    2 h
    80 &
    intermediate structure
    HBr
    CH2Cl2
    0 °C, 2 h, 80%
    intermediate structure
  • I2
    MeOH
    RT
    2 h
    66 %
    intermediate structure
    I2
    MeOH
    RT, 2 h, 66%
    intermediate structure