Methyl ether
Protection :
-
-
KOH, Me2SO4
H2O, MeOH
Reflux, 90 min, 90%
-
Me3O+BF4-, Proton Sponge
CH2Cl2
RT, 12 h, 85%
-
K2CO3, Me2SO4, NaHSO3
Acetone
RT, 3 h, 82-86%
-
KOH, Me2SO4
Acetone
RT, 15 h, 97%
-
K2CO3, Me2SO4
Acetone
Reflux, 16 h, 96%
K2CO3, Me2SO4
Acetone
Reflux, 2 h, 90%
-
MeI, NaOH, n-Bu4N+ Br-
H2O
Reflux, 30 min, 80%
Deprotection :
-
-
BBr3
CH2Cl2
0 °C to RT, 24 h, 83%
BBr3
CH2Cl2
0 °C to RT, 19 h, 90%
BBr3
CH2Cl2
-78 °C to RT, 2.5 h, 78%
BBr3
CH2Cl2
0 °C, 2 h, 80%
BBr3
CH2Cl2
-78 °C, 50 min, 88%
-
Pyr.HCl
220 °C, 6 min, 34%
-
BBr3
CHCl3
RT, 17 min, 91%
-
BCl3
CH2Cl2
0 °C, 15 min, 90%
-
NaSEt
DMF
150 °C, 16 h, 70%