Methyl ether

Methyl ether scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • Me2SO4 KOH
    MeOH H2O
    Reflux
    90 min
    90 %
    intermediate structure
    Me2SO4, KOH
    MeOH, H2O
    Reflux, 90 min, 90%
    intermediate structure
  • Me3O+BF4- Proton Sponge
    CH2Cl2
    RT
    12 h
    85 %
    intermediate structure
    Me3O+BF4-, Proton Sponge
    CH2Cl2
    RT, 12 h, 85%
    intermediate structure
  • Me2SO4 K2CO3 NaHSO3
    Acetone
    RT
    3 h
    82-86 %
    intermediate structure
    Me2SO4, K2CO3, NaHSO3
    Acetone
    RT, 3 h, 82-86%
    intermediate structure
  • Me2SO4 KOH
    Acetone
    RT
    15 h
    97 %
    intermediate structure
    Me2SO4, KOH
    Acetone
    RT, 15 h, 97%
    intermediate structure
  • Me2SO4 K2CO3
    Acetone
    Reflux
    2-16 h
    90-96 %
    intermediate structure
    Me2SO4, K2CO3
    Acetone
    Reflux, 16 h, 96%
    intermediate structure
    intermediate structure
    Me2SO4, K2CO3
    Acetone
    Reflux, 2 h, 90%
    intermediate structure
  • MeI NaOH n-Bu4N+ Br-
    H2O
    Reflux
    30 min
    80 %
    intermediate structure
    MeI, NaOH, n-Bu4N+ Br-
    H2O
    Reflux, 30 min, 80%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • BBr3
    CH2Cl2
    -78 °C - RT
    50 min - 24 h
    78-90 %
    intermediate structure
    BBr3
    CH2Cl2
    0 °C to RT, 24 h, 83%
    intermediate structure
    intermediate structure
    BBr3
    CH2Cl2
    0 °C to RT, 19 h, 90%
    intermediate structure
    intermediate structure
    BBr3
    CH2Cl2
    -78 °C to RT, 2.5 h, 78%
    intermediate structure
    intermediate structure
    BBr3
    CH2Cl2
    0 °C, 2 h, 80%
    intermediate structure
    intermediate structure
    BBr3
    CH2Cl2
    -78 °C, 50 min, 88%
    intermediate structure
  • Pyr.HCl
    N/A
    220 °C
    6 min
    34 %
    intermediate structure
    Pyr.HCl
    220 °C, 6 min, 34%
    intermediate structure
  • BBr3
    CHCl3
    RT
    17 min
    91 %
    intermediate structure
    BBr3
    CHCl3
    RT, 17 min, 91%
    intermediate structure
  • BCl3
    CH2Cl2
    0 °C
    15 min
    90 %
    intermediate structure
    BCl3
    CH2Cl2
    0 °C, 15 min, 90%
    intermediate structure
  • NaSEt
    DMF
    150 °C
    16 h
    70 %
    intermediate structure
    NaSEt
    DMF
    150 °C, 16 h, 70%
    intermediate structure