Table 1. Optimization of the Reaction Conditions.
| entry | equiv | T (°C) | solvent | time (h) | conversion (%)a |
|---|---|---|---|---|---|
| 1 | 4 | rt | MeOH | 24 | 27c |
| 2 | 8 | rt | MeOH | 24 | 60 |
| 3 | 10 | rt | MeOH | 24 | >99 |
| 4 | 4 | 50 | MeOH | 12 | >99 (91)b |
| 5 | 2 | 50 | MeOH | 12 | 45c |
| 6 | 3 | 50 | MeOH | 12 | 73c |
| 7 | 4 | 50 | EtOH | 12 | >99 |
| 8 | 4 | 50 | CH2Cl2 | 24 | |
| 9 | 4 | 50 | toluene | 24 | |
| 10 | 4 | rt | CH3CN | 2 | >99 (93)b |
| 11 | 2 | rt | CH3CN | 2 | >99 (90)b |
| 12 | 2 | rt | DMF | 12 |
Determined by 1H NMR in the crude reaction mixture.
Yield after chromatographic purification.
Nitrone is the only observed product in the 1H NMR spectra.
