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. 2018 Dec 18;3(12):17617–17628. doi: 10.1021/acsomega.8b02147

Table 3. Optimization Studiesa.

graphic file with name ao-2018-02147e_0011.jpg

entry base (equiv) time (h) solvent % yieldb
1 KOAc (1.0) 19 CH3CN 20
2 DBU (1.0) 1 CH3CN 44
3 K2CO3 (1.0) 15 CH3CN 71
4 Cs2CO3 (1.0) 15 CH3CN 57
5 NaOH (1.0) 4 CH3CN 50
6 KOtBu (1.0) 4 CH3CN 52
7 K2CO3 (1.0) 17 THF 45
8 K2CO3 (1.0) 18 CHCl3 35
9 K2CO3 (1.0) 26 toluene 30
10 K2CO3 (0.5) 23 CH3CN 47
11 K2CO3 (2.0) 12 CH3CN 55
12 K2CO3 (1.0) (LiCl)c 15 CH3CN 44
13 K2CO3(1.0) (H2O)d 8 CH3CN 76e
14 K2CO3 (1.0) 15 min CH3CN 43f
a

Reaction scale: 1a (0.23 mmol, 1.0 equiv), 5a (0.23 mmol, 1.0 equiv), and solvent (3 mL) at RT until complete consumption of at least one of the starting materials.

b

After column chromatography.

c

LiCl (0.23 mmol, 1.0 equiv).

d

CH3CN/H2O (97:3 v/v).

e

59% yield at 60 °C for 6 h.

f

Under microwave at 40 °C.