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. 2020 Apr 30;11(25):6500–6509. doi: 10.1039/d0sc01349h

Table 1. Addition of lithium N-methylanilide 2a to ethyl benzoate 1a in various molecular solvents and eutectic mixtures a .

Inline graphic
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.