Benzyl ether (Bn)

Benzyl ether (Bn) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • BnBr NaH n-Bu4N+ I-
    THF
    0 °C - RT
    4.5 h
    98 %
    intermediate structure
    BnBr, NaH, n-Bu4N+ I-
    THF
    0 °C to RT, 4.5 h, 98%
    intermediate structure
  • BnBr KH n-Bu4N+ I-
    Et2O
    RT
    2 h
    87 %
    intermediate structure
    BnBr, KH, n-Bu4N+ I-
    Et2O
    RT, 2 h, 87%
    intermediate structure
  • BnBr TMS2NK
    THF
    0 °C - RT
    20 min
    92 %
    intermediate structure
    TMS2NK, BnBr
    THF
    0 °C to RT, 20 min, 92%
    intermediate structure
  • Cl3C(=NH)OBn TfOH
    Et2O
    RT
    10 h
    100 %
    intermediate structure
    Cl3C(=NH)OBn, TfOH
    Et2O
    RT, 10 h, 100%
    intermediate structure
  • BnBr NaH
    DMF
    0 °C - RT
    19 h
    92 %
    intermediate structure
    BnBr, NaH
    DMF
    0 °C to RT, 19 h, 92%
    intermediate structure
  • BnBr K2CO3
    Acetone
    Reflux
    24 h
    92 %
    intermediate structure
    BnBr, K2CO3
    Acetone
    Reflux, 24 h, 92%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • H2 Pd/C
    EtOAc
    RT
    30 min - 30 h
    82-98 %
    intermediate structure
    H2, Pd/C
    EtOAc
    RT, 11.5 h, 85%
    intermediate structure
    intermediate structure
    H2, Pd/C
    EtOAc
    RT, 30 min, 97%
    intermediate structure
    intermediate structure
    H2, Pd/C
    EtOAc
    RT, 45 min, 82%
    intermediate structure
    intermediate structure
    H2, Pd/C
    EtOAc
    RT, 30 h, 98%
    intermediate structure
  • H2 Pd/C
    MeOH
    RT
    6 min - 20 h
    74-89 %
    intermediate structure
    H2, Pd/C
    MeOH
    RT, 6 min, 74%
    intermediate structure
    intermediate structure
    H2, Pd/C
    MeOH
    RT, 14 h, 81%
    intermediate structure
    intermediate structure
    H2, Pd/C
    MeOH
    RT, 20 h, 89%
    intermediate structure
  • H2 Pd/C
    EtOH
    RT
    3-10 h
    82-95 %
    intermediate structure
    H2, Pd/C
    EtOH
    RT, 10 h, 82%
    intermediate structure
    intermediate structure
    H2, Pd/C
    EtOH
    RT, 3 h, 95%
    intermediate structure
  • H2 Pd(OH)2/C
    EtOH
    RT
    23 h
    76 %
    intermediate structure
    H2, Pd(OH)2/C
    EtOH
    RT, 23 h, 76%
    intermediate structure
  • H2 Pd(OH)2/C
    MeOH EtOH i-PrOH
    RT
    48 h
    96 %
    intermediate structure
    H2, Pd(OH)2/C
    EtOH, MeOH, i-PrOH
    RT, 48 h, 96%
    intermediate structure
  • Li
    NH3 THF EtOH
    -33 °C
    60 min - 3.5 h
    83-90 %
    intermediate structure
    Li
    NH3, THF, EtOH
    Reflux, 60 min, 90%
    intermediate structure
  • Na
    NH3 THF
    -78 - -45 °C
    2 h
    100 %
    intermediate structure
    Na
    NH3, THF
    -78 to -45 °C, 2 h, 100%
    intermediate structure
  • H2 Pd/C
    MeOH AcOH
    RT
    20 h
    96 %
    intermediate structure
    H2, Pd/C
    MeOH, AcOH
    20 h, 96%
    intermediate structure
  • H2
    EtOAc EtOH
    RT
    5 h
    67 %
    intermediate structure
    H2, Pd(OH)2/C
    EtOAc, EtOH
    RT, 5 h, 67%
    intermediate structure
  • Li.DTBBP
    THF
    -78 °C
    3 h
    95 %
    intermediate structure
    Li.DTBBP
    THF
    -78 °C, 3 h, 95%
    intermediate structure