Methyl ether

Methyl ether scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • MeI NaH
    THF
    0 °C - RT
    60 min
    96 %
    intermediate structure
    NaH, MeI
    THF
    0 °C to RT, 60 min, 96%
    intermediate structure
  • MeI KH
    THF
    RT - Reflux
    2 h
    90 %
    intermediate structure
    KH, MeI
    THF
    RT to Reflux, 2 h, 90%
    intermediate structure
  • MeI KH 18-Crown-6
    THF
    0 °C - RT
    2 d
    77 %
    intermediate structure
    KH, 18-Crown-6, MeI
    THF
    0 °C to RT, 2 d, 77%
    intermediate structure
  • MeI Ag2O CaSO4
    N/A
    RT
    20 h
    96 %
    intermediate structure
    MeI, Ag2O, CaSO4
    RT, 20 h, 96%
    intermediate structure
  • MeOTf 2,6-Di-tert-butylpyridine
    CH2Cl2
    RT
    40 h
    85 %
    intermediate structure
    MeOTf, 2,6-Di-tert-butylpyridine
    CH2Cl2
    RT, 40 h, 85%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TMSCl NaI
    MeCN H2O
    40 °C
    15 h
    97 %
    intermediate structure
    TMSCl, NaI
    MeCN, H2O
    40 °C, 15 h, 97%
    intermediate structure
  • TMSI
    MeCN
    60 °C
    48 h
    95 %
    intermediate structure
    TMSI
    MeCN
    60 °C, 48 h, 95%
    intermediate structure