Table 1. Optimization Studies for the One-Step Synthesis of Indium Stearate (3a)a.
entry | base | equiv | temp (°C) | time (h) | yield (%) |
---|---|---|---|---|---|
1 | DABCO | 4.0 | reflux | overnight | 72 |
2 | pyridine | 4.0 | reflux | overnight | 66 |
3 | triethylamine | 4.0 | reflux | overnight | 32 |
4a | DBU | 4.0 | reflux | overnight | 78 |
5b | DBU | 3.0 | reflux | overnight | 80 |
6c | DBU | 1.0 | reflux | overnight | 85 |
7d | DBU | 0.5 | reflux | overnight | 66 |
8e | DBU | 1.0 | 25 | overnight | nr |
9f | DBU | 1.0 | 40 | overnight | 22 |
10g | DBU | 1.0 | 60 | overnight | 60 |
11 | DBU | 1.0 | reflux | 6 h | 60 |
12 | DBU | 1.0 | reflux | 8 h | 58 |
13 | DBN | 1.0 | reflux | overnight | 82 |
Unless otherwise noted, all reactions were carried out with 4.0 equiv (with respect to a fatty acid) of the base under reflux conditions.
The reaction was performed with 3.0 equiv of the base.
The reaction was performed with 1.0 equiv of the base.
The reaction was performed with 0.5 equiv of the base.
nr denotes no reaction.
The reaction was performed at 40 °C.
The reaction was performed at 60 °C.