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 %

BnBr, NaH, n-Bu4N+ I-

THF

0 °C to RT, 4.5 h, 98%
BnBr KH n-Bu4N+ I-

Et2O

RT

2 h

87 %

BnBr, KH, n-Bu4N+ I-

Et2O

RT, 2 h, 87%
BnBr TMS2NK

THF

0 °C - RT

20 min

92 %

BnBr, TMS2NK

THF

0 °C to RT, 20 min, 92%
TfOH Cl3C(=NH)OBn

Et2O

RT

10 h

100 %

TfOH, Cl3C(=NH)OBn

Et2O

RT, 10 h, 100%
BnBr NaH

DMF

0 °C - RT

19 h

92 %

BnBr, NaH

DMF

0 °C to RT, 19 h, 92%
BnBr K2CO3

Acetone

Reflux

24 h

92 %

BnBr, K2CO3

Acetone

Reflux, 24 h, 92%

Deprotection :

Reagents

Solvents

Temperature

Time

Yield
H2 Pd/C

EtOAc

RT

30 min - 30 h

82-98 %

H2, Pd/C

EtOAc

RT, 11.5 h, 85%

H2, Pd/C

EtOAc

RT, 30 min, 97%

H2, Pd/C

EtOAc

RT, 45 min, 82%

H2, Pd/C

EtOAc

RT, 30 h, 98%
H2 Pd/C

MeOH

RT

6 min - 20 h

74-89 %

H2, Pd/C

MeOH

RT, 6 min, 74%

H2, Pd/C

MeOH

RT, 14 h, 81%

H2, Pd/C

MeOH

RT, 20 h, 89%
H2 Pd/C

EtOH

RT

3-10 h

82-95 %

H2, Pd/C

EtOH

RT, 10 h, 82%

H2, Pd/C

EtOH

RT, 3 h, 95%
H2 Pd(OH)2/C

EtOH

RT

23 h

76 %

H2, Pd(OH)2/C

EtOH

RT, 23 h, 76%
H2 Pd(OH)2/C

EtOH i-PrOH MeOH

RT

48 h

96 %

H2, Pd(OH)2/C

EtOH, i-PrOH, MeOH

RT, 48 h, 96%
Li

EtOH NH3 THF

-33 °C

60 min - 3.5 h

83-90 %

Li

EtOH, NH3, THF

Reflux, 60 min, 90%
Na

NH3 THF

-78 - -45 °C

2 h

100 %

Na

NH3, THF

-78 to -45 °C, 2 h, 100%
H2 Pd/C

AcOH MeOH

RT

20 h

96 %

H2, Pd/C

AcOH, MeOH

20 h, 96%
H2

EtOAc EtOH

RT

5 h

67 %

H2, Pd(OH)2/C

EtOAc, EtOH

RT, 5 h, 67%
Li.DTBBP

THF

-78 °C

3 h

95 %

Li.DTBBP

THF

-78 °C, 3 h, 95%