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. 2024 Mar 21;9(13):15328–15338. doi: 10.1021/acsomega.3c10080

Table 1. Optimization of the Wittig Reaction for 7a.

graphic file with name ao3c10080_0008.jpg

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
a

Reactions were performed with 1.0 or 1.5 equiv of Wittig reagents 6 under the given conditions.

b

Isolated yields.