Triethylsilyl ether (TES)

Triethylsilyl ether (TES) scheme

Protection :

Reagents

Solvents

Temperature

Time

Yield
TESCl

Pyr

-78 °C - RT

30 min - 12 h

85-92 %

TESCl

Pyr

RT, 12 h, 85%

TESCl

Pyr

RT, 30 min, 87%

"92 % yield based on 95 % conversion."
Imidazole TESCl

DMF

0 °C

60 min

99 %

Imidazole, TESCl

DMF

0 °C, 60 min, 99%
DMAP Imidazole TESCl

DMF

0 °C - RT

16 h

85 %

DMAP, Imidazole, TESCl

DMF

0 °C to RT, 16 h, 85%
2,6-Lutidine TESOTf

CH2Cl2

0 °C - RT

30 min

83-92 %

2,6-Lutidine, TESOTf

CH2Cl2

0 °C, 30 min, 92%

2,6-Lutidine, TESOTf

CH2Cl2

RT, 30 min, 83%
Et3N TESOTf

CH2Cl2

-78 °C

30 min

92 %

Et3N, TESOTf

CH2Cl2

-78 °C, 30 min, 92%
TESOTf

Pyr

-23 °C

10 min

98 %

TESOTf

Pyr

-23 °C, 10 min, 98%
Pyr TESCl

CH2Cl2

-78 - -20 °C

10 h

92 %

Pyr, TESCl

CH2Cl2

-78 to -20 °C, 10 h, 92%
i-Pr2NEt TESOTf

CH2Cl2

-60 - 0 °C

2.5 h

71 %

i-Pr2NEt, TESOTf

CH2Cl2

-60 to 0 °C, 2.5 h, 71%

Deprotection :

Reagents

Solvents

Temperature

Time

Yield
Pyr.HF

THF

0 °C - RT

60 min - 72 h

80-100 %

Pyr.HF

THF

RT, 90 min, 80%

Pyr.HF

THF

RT, 2 h, 88%

Pyr.HF

THF

RT, 60 min, 96%

Pyr.HF

THF

RT, 72 h, 100%

Pyr.HF

THF

0 °C, 4 h, 93%
Pyr.HF

MeCN

0 °C

11 h

100 %

Pyr.HF

MeCN

0 °C, 11 h, 100%
n-Bu4N+ F-

THF

-78 °C - RT

2 - 4 h

72-88 %

n-Bu4N+ F-

THF

-78 °C, 4 h, 72%

n-Bu4N+ F-

THF

-50 °C to RT, 2 h, 88%
AcOH n-Bu4N+ F-

THF

RT

18 h

87 %

AcOH, n-Bu4N+ F-

THF

RT, 18 h, 87%
HCl

H2O THF

RT

60 min

89 %

HCl

H2O, THF

RT, 60 min, 89%
CF3CO2H

H2O MeCN

0 °C

4 h

93 %

CF3CO2H

H2O, MeCN

0 °C, 4 h, 93%
K2CO3

MeOH

0 °C - RT

13 h

92 %

K2CO3

MeOH

0 °C to RT, 13 h, 92%