Table 1. Synthesis of Cyclohexenones in Water.
| Entry | Synthesis of | Conditionsa | Yield (%) (anti:syn) |
|---|---|---|---|
| 1 | 1b | H2O, 135 °C | 96 (64:36) |
| 2 | 13 | H2O, 135 °C | 98 (72:28) |
| 3 | 14 | H2O, 135 °C | 98 (75:25) |
| 4 | 15 | H2O, 135 °C | 90 (15a:15b 67:33), no syn products |
| 5 | 12 | H2O, 135 °C | 83 (62:38) |
| 6 | 1b | H2O, RTc | 96 (1A, 100:0) |
| 7 | 1b | Brine,d 135 °C | 94 (95:5) |
Reaction conditions: α-ketoacid (2.0 mmol), benzaldehyde (2.0 mmol), ketone (2.0 mmol), NaOH (3 mmol, 10 M at H2O solution), H2O (3 mL); microwave vial was heated to 135 °C and heat was maintained for 30 min.
4-Phenyl-3-buten-2-one (2 mmol) is used instead of benzaldehyde and ketone.
Reaction was stirred for 4 h at room temperature at 20 mL vial.
Brine solution (3 mL, saturated NaCl solution) was used instead of Milli-Q H2O.