Benzyl ether (Bn)

Benzyl ether (Bn) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • BnBr K2CO3
    MeCN
    82 °C
    4 h
    88 %
    intermediate structure
    BnBr, K2CO3
    MeCN
    82 °C, 4 h, 88%
    intermediate structure
  • BnBr K2CO3 n-Bu4N+ I-
    DMF
    RT
    6 h
    93 %
    intermediate structure
    BnBr, K2CO3, n-Bu4N+ I-
    DMF
    RT, 6 h, 93%
    intermediate structure
  • BnBr Ag2O
    CH2Cl2
    RT
    18 h
    92 %
    intermediate structure
    BnBr, Ag2O
    CH2Cl2
    RT, 18 h, 92%
    intermediate structure
  • BnBr K2CO3
    Acetone
    RT - Reflux
    2 - 6 h
    92 - 95 %
    intermediate structure
    BnBr, K2CO3
    Acetone
    RT, 6 h, 95%
    intermediate structure
    intermediate structure
    BnBr, K2CO3
    Acetone
    Reflux, 2 h, 92%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • H2 Pd/C
    EtOAc AcOH
    RT
    3 h
    99 %
    intermediate structure
    H2, Pd/C
    EtOAc, AcOH
    RT, 3 h, 99%
    intermediate structure
  • H2 Pd/C
    EtOAc
    RT
    9 h
    99 %
    intermediate structure
    H2, Pd/C
    EtOAc
    RT, 9 h, 99%
    intermediate structure
  • HBr
    CH2Cl2
    0 °C
    2 h
    80 %
    intermediate structure
    HBr
    CH2Cl2
    0 °C, 2 h, 80%
    intermediate structure
  • Ni (Raney)
    EtOH
    Reflux
    5 h
    93 %
    intermediate structure
    Ni (Raney)
    EtOH
    Reflux, 5 h, 93%
    intermediate structure