Table 1. Addition of lithium N-methylanilide 2a to ethyl benzoate 1a in various molecular solvents and eutectic mixtures a .
| |||
| Entry | Solvent | LiNMePh b [eq.] | Yield c [%] |
| 1 | THF d | 2 | 93 |
| 2 | 2-MeTHF | 3 | 80 |
| 3 | 2 | 81 | |
| 4 | 1.5 | 80 | |
| 5 | 1 | 78 | |
| 6 | 1ChCl/2Gly | 3 | 83 |
| 7 | 1ChCl/2EG | 3 | 59 |
| 8 | 1ChCl/2H2O | 3 | 81 |
| 9 | 1LiCl/3Gly e | 3 | 79 |
| 10 | H2O | 3 | 36 |
| 11 | Gly | 3 | 85 |
| 12 | 1.5 | 79 | |
aReactions performed in air at ambient temperature using 1 g of solvent and 1 mmol of ester. Reactions stirred for 20 s, then quenched with sat. Rochelle's salt soln. (5 mL).
bLithium amide was added as a 1 M soln. in 2-MeTHF.
cIsolated yields are given.
dLithium amide 2a was added as a 0.2 M soln. in THF.
eReactions carried out at 53 °C due to viscosity issues.