Williamson Ether Synthesis

Mechanism of the Williamson Ether Synthesis

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Sample reactions

KOH, Me2SO4
H2O, MeOH
Reflux, 90 min, 90%


Na2CO3
THF
Reflux, , 80% (2 steps)


BnBr, TMS2NK
THF
0 °C to RT, 20 min, 92%


MeI, NaH
DMF
0 °C to RT, 2 h, 93% (3 steps)


BnBr, KH, n-Bu4N+ I-
Et2O
RT, 2 h, 87%


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


BnBr, K2CO3, n-Bu4N+ I-
DMF
RT, 6 h, 93%


BnBr, K2CO3, n-Bu4N+ I-
DMF
RT, 53 h, 50-57%


NaH, AllylBr
PhH
70 °C, 3.5 h


Me2CuLi, AllylCl
HMPA, THF
-78 °C to RT


BnBr, TMS2NNa, n-Bu4N+ I-
THF
0 °C to RT, 70 min


NaH, n-Bu4N+ I-, 2-Bromomethylnaphthalene
DMF
0 °C to RT, 36 h, 96%


KH, MeI, 18-Crown-6
THF
0 °C to RT, 2 d, 77%


MeI, NaH
DMF
-15 °C, 60 min, 82% (2 steps)


KH, MeI
THF
RT to Reflux, 2 h, 90%


K2CO3, Me2SO4, NaHSO3
Acetone
RT, 3 h, 82-86%



KOt-Bu
DMSO
50 °C, 5 h


K2CO3, Me2SO4
Acetone
Reflux, 16 h, 96%



NaH
DMF


MeI, NaH
THF
0 °C to RT, 60 min, 96%


BnBr, NaH
DMF
0 °C to RT, 19 h, 92%



KH
THF
0 °C to RT, 90 min, 60%


K2CO3, Me2SO4
Acetone
Reflux, 2 h, 90%


K2CO3, Me2SO4
Acetone
80 °C, 60 min, 90% (2 steps)



K2CO3
Acetone
Reflux, 8 h, 66%


BnBr, K2CO3
Acetone
RT, 6 h, 95%


K2CO3, MeI
DMF
RT, 60 min, 87%


BnBr, K2CO3
Acetone
Reflux, 2 h, 92%


BnBr, NaH
DMF
RT, , 99%


Me2SO4, NaOH
H2O
RT to 100 °C


K2CO3, MeI
DMF
RT, 18 h, 45% (2 steps)


K2CO3, MeI
DMF
RT, 24 h, 99%


KOH, Et2SO4
H2O
100 °C, 30 min, 68%


K2CO3, MeI
Acetone
RT, 6 h, 85%


KH, n-Bu3SnCH2I
THF
RT, 3.5 h, 95%


LiOH, Me2SO4
THF
50 °C, 3 h, 86%


BnBr, K2CO3
CHCl3, MeOH
Reflux, 4 h, 71%


K2CO3, MeI
Acetone
Reflux, , 84%
