Benzoate (Bz)

Benzoate (Bz) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • BzCl Pyr
    CH2Cl2
    RT
    3 h
    96 %
    intermediate structure
    BzCl, Pyr
    CH2Cl2
    RT, 3 h, 96%
    intermediate structure
  • BzCl
    Pyr
    RT - 70 °C
    4 - 24 h
    78-90 %
    intermediate structure
    BzCl
    Pyr
    70 °C, 24 h, 78%
    intermediate structure
    intermediate structure
    BzCl
    Pyr
    RT, 4 h, 90%
    intermediate structure
  • BzCl Et3N DMAP
    CH2Cl2
    0 °C - RT
    30 min
    82 %
    intermediate structure
    BzCl, Et3N, DMAP
    CH2Cl2
    0 °C to RT, 30 min, 82%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • K2CO3
    MeOH
    RT
    60 min - 2 h
    94-95 %
    intermediate structure
    K2CO3
    MeOH
    RT, 60 min, 94%
    intermediate structure
    intermediate structure
    K2CO3
    MeOH
    RT, 2 h, 95%
    intermediate structure
  • K2CO3
    MeOH THF
    RT
    2 h
    81 %
    intermediate structure
    K2CO3
    MeOH, THF
    RT, 2 h, 81%
    intermediate structure
  • KOH
    EtOH
    RT
    20 min
    80 %
    intermediate structure
    KOH
    EtOH
    RT, 20 min, 80%
    intermediate structure
  • KCN
    EtOH
    0 °C
    3 h
    68 %
    intermediate structure
    KCN
    EtOH
    0 °C, 3 h, 68%
    "76 % yield based on 89 % conversion."
    intermediate structure