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. 2022 Jun 1;12(26):16342–16353. doi: 10.1039/d2ra02205b

Optimizing of the reaction conditions for the synthesis of 2ha.

graphic file with name d2ra02205b-u2.jpg
Entry Solvent Temperature (°C) Catalyst loading (mg) Time (min) Yieldb (%)
1 90 10 10 92
2 80 15 10 90
3c 70 10 10 91
4 70 5 30 80
5 70 10 Trace
6 70 7 10 82
7 70 20 10 92
8 70 120 60
9 60 10 30 70
10 50 10 100 20
11 H2O Reflux 10 60
12 EtOH Reflux 10 60 45
13 n-Hexane Reflux 10 60
14 EtOAc Reflux 10 60 50
15 CH2Cl2 Reflux 10 60
a

Reaction conditions: 4-cholorobenzaldehyde (1 mmol, 0.140 g), 5,5-dimethylcyclohexane-1,3-dione (1 mmol, 0.140), ethyl acetoacetate (1 mmol, 0.130 g), ammonium acetate (1 mmol, 0.078 g).

b

Related to isolated yields.

c

Optimal data.