Table 2.
Effect of the solvent on the reactiona
Entry | Solvent | Yield (%) | Snyder polarity indexb |
---|---|---|---|
1 | CHCl3 | 62 | 4.1 |
2 | CH2Cl2 | 58 | 3.1 |
3 | DCE | 46 | 3.5 |
4 | EtOAc | 16 | 4.4 |
5 | DMF | 0 | 6.4 |
6 | NMP | 0 | 6.7 |
7 | MeCN | 10 | 5.8 |
8 | Et2O | 54 | 2.8 |
9 | CPMEc | 38 | Not available |
10 | THF | 21 | 4.0 |
11 | 1,4-Dioxane | 0 | 4.8 |
12 | Toluene | 66 | 2.4 |
Monitored by TLC, product isolated by radial-band chromatography and the structure confirmed by NMR spectroscopy.
Polarity is indicated by the Snyder Polarity Index.26
CMPE-cyclopentyl methyl ether.