Benzyl ether (Bn)

Benzyl ether (Bn) scheme

Protection :

Reagents

Solvents

Temperature

Time

Yield
BnBr K2CO3

MeCN

82 °C

4 h

88 %

BnBr, K2CO3

MeCN

82 °C, 4 h, 88%
BnBr K2CO3 n-Bu4N+ I-

DMF

RT

6 h

93 %

BnBr, K2CO3, n-Bu4N+ I-

DMF

RT, 6 h, 93%
BnBr Ag2O

CH2Cl2

RT

18 h

92 %

BnBr, Ag2O

CH2Cl2

RT, 18 h, 92%
BnBr K2CO3

Acetone

RT - Reflux

2 - 6 h

92 - 95 %

BnBr, K2CO3

Acetone

RT, 6 h, 95%

BnBr, K2CO3

Acetone

Reflux, 2 h, 92%

Deprotection :

Reagents

Solvents

Temperature

Time

Yield
H2 Pd/C

AcOH EtOAc

RT

3 h

99 %

H2, Pd/C

AcOH, EtOAc

RT, 3 h, 99%
H2 Pd/C

EtOAc

RT

9 h

99 %

H2, Pd/C

EtOAc

RT, 9 h, 99%
HBr

CH2Cl2

0 °C

2 h

80 %

HBr

CH2Cl2

0 °C, 2 h, 80%
Ni (Raney)

EtOH

Reflux

5 h

93 %

Ni (Raney)

EtOH

Reflux, 5 h, 93%