Table 1. Optimization of the Wittig Reaction for 7a.
| entry | 6 (equiv) | R | solvent | temp. (°C) | time (h) | yield (%)b |
|---|---|---|---|---|---|---|
| 1 | 6a (1.0) | H | DCM | 25 | 12 | 35 |
| 2 | 6a (1.5) | H | DCM | 25 | 12 | 42 |
| 3 | 6a (1.5) | H | DCM | 0 | 24 | 65 |
| 4 | 6a (1.5) | H | DCM | –20 | 48 | 0 |
| 5 | 6a (1.5) | H | Et2O | 0 | 24 | 62 |
| 6 | 6a (1.5) | H | THF | 0 | 24 | 58 |
| 7 | 6a (1.5) | H | DMF | 0 | 24 | 47 |
| 8 | 6b (1.5) | 4-F | DCM | 0 | 24 | 62 |
| 9 | 6c (1.5) | 3-F | DCM | 0 | 24 | 71 |
| 10 | 6d (1.5) | 4-Cl | DCM | 0 | 24 | 52 |
| 11 | 6e (1.5) | 4-Br | DCM | 0 | 24 | 58 |
| 12 | 6f (1.5) | 4-CH3O | DCM | 0 | 24 | 84 |
| 13 | 6g (1.5) | 3-CH3O | DCM | 0 | 24 | 72 |
| 14 | 6h (1.5) | 4-CH3 | DCM | 0 | 24 | 57 |
Reactions were performed with 1.0 or 1.5 equiv of Wittig reagents 6 under the given conditions.
Isolated yields.
