Methyl ester

Methyl ester scheme

Protection :

Reagents

Solvents

Temperature

Time

Yield
CH2N2

Et2O

RT

1 min - 3 h

92-100 %

CH2N2

Et2O, MeOH

RT, 90 min, 92%

CH2N2

Et2O

RT, 1 min, 100%

CH2N2

Et2O

RT, 3 h, 93%
CH2N2

MeOH

RT

60 min

84 %

CH2N2

MeOH

RT, 60 min, 84%

Deprotection :

Reagents

Solvents

Temperature

Time

Yield
LiOH

H2O THF

0 °C - RT

60 min - 20 h

75 - 100 %

LiOH

H2O, THF

RT, 12 h, 100%

LiOH

H2O, THF

RT, 20 h, 100%

LiOH

H2O, THF

0 °C, 60 min, 100%

LiOH

H2O, THF

RT, 5 h, 75%

LiOH

H2O, THF

RT, ON, 93%
LiOH

MeOH THF

RT

ON

97 %

LiOH

MeOH, THF

RT, ON, 97%
NaOH

H2O MeOH

RT - Reflux

4 - 17 h

99 %

NaOH

H2O, MeOH

RT, 17 h, 99%

NaOH

H2O, MeOH

Reflux, 4 h, 99%
KOH

H2O MeOH

RT - 90 °C

60 min - 48 h

98-100 %

KOH

H2O, MeOH

Reflux, 2 h, 100%

KOH

H2O, MeOH

Reflux, 12 h, 100%

KOH

H2O, MeOH

90 °C, 48 h, 98%
KOH

MeOH

Reflux

90 min

100 %

KOH

MeOH

Reflux, 90 min, 100%
KOH

EtOH H2O

RT - Reflux

6 - 20 h

91-100 %

KOH

EtOH, H2O

Reflux, 6 h, 91%

KOH

EtOH, H2O

RT, 20 h, 100%
MeSnOH

DCE

75 °C

48 h

78 %

MeSnOH

DCE

75 °C, 48 h, 78%
NaOH

H2O THF

5 °C

ON

96 %

NaOH

H2O, THF

5 °C, ON, 96%
KOH

Ethylene Glycol H2O

140 °C

2 h

84 %

KOH

Ethylene Glycol, H2O

140 & deg;C, 2 h, 84%
LiOH

H2O MeCN

70 °C

4 h

73 %

LiOH

H2O, MeCN

70 °C, 4 h, 73%
LiOH

H2O MeOH

RT

5 h

95 %

LiOH

H2O, MeOH

RT, 5 h, 95%