Optimization of reaction parametersa.
Entry | Solvent | Base (mol%) | T (°C) | Yieldb (%) |
---|---|---|---|---|
1 | CH2Cl2 | Na2CO3 (50 mol%) | 60 | 80 |
2 | Toluene | Na2CO3 (50 mol%) | 60 | 54 |
3 | 1,4-Dioxane | Na2CO3 (50 mol%) | 60 | 81 |
4 | MeOH | Na2CO3 (50 mol%) | 60 | Mixture |
5 | ClCH2CH2Cl | Na2CO3 (50 mol%) | 60 | 86 |
6 | ClCH2CH2Cl | K2CO3 (50 mol%) | 60 | 72 |
7 | ClCH2CH2Cl | Li2CO3 (50 mol%) | 60 | 79 |
8 | ClCH2CH2Cl | K3PO4 (34 mol%) | 60 | 67 |
9 | ClCH2CH2Cl | Et3N (100 mol%) | 60 | 83 |
10 | ClCH2CH2Cl | Na2CO3 (50 mol%) | 30 | 83 |
11c | ClCH2CH2Cl | Na2CO3 (50 mol%) | 30 | 92 |
Reaction conditions: 1a (0.5 mmol), TMSCN (1.0 mol), 3 mL of solvents, 24 h.
Isolated yield.
KF (1.0 mol) was added as additive.