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. 2020 Apr 7;5(15):8515–8522. doi: 10.1021/acsomega.9b04038

Table 2. Optimization of the Synthesis of Compound 6a.

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entry solvent catalyst (mol %) time (min) temp (°C) % yield 6aa
1 DCM Grubbs I (5) 5 RT 87
2 DCM Grubbs I (5) 10 RT 89
3 DCM Grubbs I (5) 15 RT 89
4 DCM Grubbs II (5) 3 RT 90
5 DCM Grubbs II (5) 5 RT 92
6 DCM Grubbs II (5) 10 RT 92
7 toluene Grubbs II (5) 3 RT 98
8 THF Grubbs II (5) 3 RT 93
9 toluene Grubbs II (5) 5 50 98
10 toluene Grubbs II (5) 5 100 98
11 toluene Grubbs II (5) 30 120 92
12 toluene Grubbs II (3) 3 RT 98b
13 toluene Grubbs II (10) 3 RT 98
a

Isolated yield.

b

Optimized condition.